Iron (Iii) Tosylate Catalyzed Synthesis Of 3,4-Dihydropyrimidin-2(1h)-Ones/Thiones, Ram S. Mohan, Jacob T. Starcevich, Thomas J. Laughlin
Dec 2012
Iron (Iii) Tosylate Catalyzed Synthesis Of 3,4-Dihydropyrimidin-2(1h)-Ones/Thiones, Ram S. Mohan, Jacob T. Starcevich, Thomas J. Laughlin
Ram S. Mohan
No abstract provided.
Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram S. Mohan, Neil J. Baldwin, Anna N. Nord, Brendan D. O’Donnell
Dec 2011
Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram S. Mohan, Neil J. Baldwin, Anna N. Nord, Brendan D. O’Donnell
Ram S. Mohan
Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.
A Mild And Chemoselective Method For The Deprotection Of Tert-Butyldimethylsilyl (Tbdms) Ethers Using Iron(Iii) Tosylate As A Catalyst, Ram S. Mohan, Jason M. Bothwell, Veronica V. Angeles, James P. Carolan, Margaret E. Olson
Dec 2009
A Mild And Chemoselective Method For The Deprotection Of Tert-Butyldimethylsilyl (Tbdms) Ethers Using Iron(Iii) Tosylate As A Catalyst, Ram S. Mohan, Jason M. Bothwell, Veronica V. Angeles, James P. Carolan, Margaret E. Olson
Ram S. Mohan
The most common method for the deprotection ofTBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F(TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection ofTBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.
Iron(Iii) Tosylate-Catalyzed Deprotection Of Aromatic Acetals In Water, Ram S. Mohan, Margaret E. Olson, James P. Carolan, Michael V. Chiodo, Phillip R. Lazzara
Dec 2009
Iron(Iii) Tosylate-Catalyzed Deprotection Of Aromatic Acetals In Water, Ram S. Mohan, Margaret E. Olson, James P. Carolan, Michael V. Chiodo, Phillip R. Lazzara
Ram S. Mohan
The deprotection of aromatic as well as conjugated acetals and ketals in water is catalyzed by iron(III) tosylate (1.0–5.0 mol %). Iron(III) tosylate is an inexpensive and readily available catalyst. The use of water, the most environmentally benign solvent, makes this procedure especially attractive for acetal deprotection.
In Your Element: Green Bismuth, Ram S. Mohan
Dec 2009
In Your Element: Green Bismuth, Ram S. Mohan
Ram S. Mohan
No abstract provided.
Bismuth(Iii) Bromide In Organic Synthesis. A Catalytic Method For The Allylation Of Tetrahydrofuranyl And Tetrahydropyranyl Ethers, Ram S. Mohan, Scott W. Krabbe, Veronica V. Angeles
Dec 2009
Bismuth(Iii) Bromide In Organic Synthesis. A Catalytic Method For The Allylation Of Tetrahydrofuranyl And Tetrahydropyranyl Ethers, Ram S. Mohan, Scott W. Krabbe, Veronica V. Angeles
Ram S. Mohan
A bismuth bromide-catalyzed (10.0 mol %) multicomponent reaction involving the allylation of THF- and THP-ethers, followed by in situ derivatization with acetic anhydride to generate highly functionalized esters has been developed under solvent-free conditions. To the best of our knowledge, this is the first report of a catalytic procedure for the allylation of THF- and THP-ethers to yield ring-opened products.
Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth(Iii) Bromide Catalyzed Synthesis Of Substituted Tetrahydroquinoline Derivatives, Ram S. Mohan, Jamie L. Rogers, Justin J. Ernat, Herbie Yung
Dec 2008
Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth(Iii) Bromide Catalyzed Synthesis Of Substituted Tetrahydroquinoline Derivatives, Ram S. Mohan, Jamie L. Rogers, Justin J. Ernat, Herbie Yung
Ram S. Mohan
The bismuth bromide catalyzed synthesis of a range of substituted tetrahydroquinoline derivatives via a three component coupling reaction between substituted anilines and enol ethers is reported. Bismuth compounds are attractive for use as catalysts because of their remarkably low toxicity. Bismuth bromide is relatively inexpensive and easy to handle, and hence preferable to other corrosive catalysts previously used for synthesis of tetrahydroquinoline derivatives.
The Discovery-Oriented Approach To Organic Chemistry. 7. Rearrangement Of Trans-Stilbene Oxide With Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram S. Mohan, James E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung
Aug 2008
The Discovery-Oriented Approach To Organic Chemistry. 7. Rearrangement Of Trans-Stilbene Oxide With Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram S. Mohan, James E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung
Ram S. Mohan
A microscale discovery-oriented experiment illustrating the rearrangement of trans-stilbene oxide using non-corrosive metal triflates as catalysts has been developed. The use of CDCl3 as the reaction solvent eliminates the need for any workup and avoids the use of highly toxic boron trifluoride etherate as a catalyst and additional reaction solvent.
Environmentally Friendly Organic Synthesis Using Bismuth Compounds: Bismuth(Iii) Iodide Catalyzed Deprotection Of Acetals In Water, Ram S. Mohan, Aaron D. Bailey, Ashvin R. Baru, Kendall K. Tashe
Dec 2007
Environmentally Friendly Organic Synthesis Using Bismuth Compounds: Bismuth(Iii) Iodide Catalyzed Deprotection Of Acetals In Water, Ram S. Mohan, Aaron D. Bailey, Ashvin R. Baru, Kendall K. Tashe
Ram S. Mohan
The chemoselective deprotection of a wide range of acetals and ketals in water is catalyzed by bismuth(III) iodide. Bismuth(III) compounds are remarkably nontoxic and hence are attractive as environmentally friendly catalysts.
Iron(Iii) P-Toluenesulfonate Catalyzed Synthesis Of Homoallyl Ethers From Acetals And Aldehydes, Ram S. Mohan, Matthew J. Spafford, Erin D. Anderson, Joshua R. Lacey, Ann C. Palma
Dec 2006
Iron(Iii) P-Toluenesulfonate Catalyzed Synthesis Of Homoallyl Ethers From Acetals And Aldehydes, Ram S. Mohan, Matthew J. Spafford, Erin D. Anderson, Joshua R. Lacey, Ann C. Palma
Ram S. Mohan
Iron(III) p-toluenesulfonate, Fe(OTs)3.6H20, is an inexpensive, versatile and commercially available catalyst for the allylation of acetals using allyltrimethylsilane to yield homoallyl ethers in moderate to good yields. The one-pot conversion of aldehydes to homoallyl ethers using alkoxysilanes has also been accomplished using Fe(OTs)3.6H20 as a catalyst. The use of mild reaction conditions and a relatively non-corrosive catalyst make this method an attractive option for the synthesis of a range of homoallyl ethers.
Reactivity Of Ionic Liquids, Ram S. Mohan, Shahana Chowdhury, Janet L. Scott
Dec 2006
Reactivity Of Ionic Liquids, Ram S. Mohan, Shahana Chowdhury, Janet L. Scott
Ram S. Mohan
Ionic liquids are becoming widely used in synthetic organic chemistry and yet relatively little attention has been paid to the intrinsic reactivity of these low temperature molten salts. Clues to the non-innocent nature of many ionic liquids are contained in the reports of altered reactivity of dissolved substrates, unexpected catalytic activity and unforeseen by-product formation. In this review, we focus on the reactivity of ionic liquids, as opposed to reactivity in ionic liquids (although discussion of the latter is often included where it aids understanding of the former).
Environment Friendly Organic Synthesis Using Bismuth Compounds. An Efficient Method For Carbonyl-Ene Reactions Catalyzed By Bismuth Triflate, Ram S. Mohan, Erin D. Anderson, Justin J. Ernat, Mai P. Nguyen, Ann C. Palma
Dec 2004
Environment Friendly Organic Synthesis Using Bismuth Compounds. An Efficient Method For Carbonyl-Ene Reactions Catalyzed By Bismuth Triflate, Ram S. Mohan, Erin D. Anderson, Justin J. Ernat, Mai P. Nguyen, Ann C. Palma
Ram S. Mohan
Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.
A Study Of Epoxyolefin Cyclizations Catalyzed By Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram S. Mohan, Joshua R. Lacey, Peter W. Anzalone, Christopher M. Duncan, Matthew J. Hackert
Dec 2004
A Study Of Epoxyolefin Cyclizations Catalyzed By Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram S. Mohan, Joshua R. Lacey, Peter W. Anzalone, Christopher M. Duncan, Matthew J. Hackert
Ram S. Mohan
Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products.
The Discovery-Oriented Approach To Organic Chemistry. 6. Selective Reduction In Organic Chemistry: Reduction Of Aldehydes In The Presence Of Esters Using Sodium Borohydride, Ram S. Mohan, Ashvin R. Baru
Dec 2004
The Discovery-Oriented Approach To Organic Chemistry. 6. Selective Reduction In Organic Chemistry: Reduction Of Aldehydes In The Presence Of Esters Using Sodium Borohydride, Ram S. Mohan, Ashvin R. Baru
Ram S. Mohan
Chemoselective reductions are valuable in organic synthesis and are routinely discussed in a sophomore organic chemistry course. Yet, there are few examples of laboratory experiments that illustrate such chemoselectivity. A reaction that is routinely discussed in sophomore organic chemistry is the selective reduction of aldehydes and ketones using sodium borohydride. Esters are typically not affected by NaBH4. However, none of the lab experiments reported to date illustrate this chemoselectivity (1). We have developed a discovery-oriented lab experiment that illustrates the chemoselective nature of reductions using sodium borohydride. The experiments involve the reduction of vanillin acetate (Scheme I) and methyl …
Environment-Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Triflate Catalyzed Synthesis Of Substituted 3,4-Dihydro-2h-L-Benzopyrans, Ram S. Mohan, Mai P. Nguyen, Joshua N. Arnold, Katherine E. Peterson
Dec 2003
Environment-Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Triflate Catalyzed Synthesis Of Substituted 3,4-Dihydro-2h-L-Benzopyrans, Ram S. Mohan, Mai P. Nguyen, Joshua N. Arnold, Katherine E. Peterson
Ram S. Mohan
A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano [2,3,b]benzopyran has also been achieved. Bi(OTf)3.xH2O (1< x < 4) (0.1mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1-benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.
Bismuth Compounds In Organic Synthesis. Bismuth Nitrate Catalyzed Chemoselective Synthesis Of Acylals From Aromatic Aldehydes, Ram S. Mohan, David H. Aggen, Joshua N. Arnold, Patrick D. Hayes, Nathaniel J. Smoter
Dec 2003
Bismuth Compounds In Organic Synthesis. Bismuth Nitrate Catalyzed Chemoselective Synthesis Of Acylals From Aromatic Aldehydes, Ram S. Mohan, David H. Aggen, Joshua N. Arnold, Patrick D. Hayes, Nathaniel J. Smoter
Ram S. Mohan
1Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 3–10 mol% Bi(NO3)3•5H2O. Ketones are not affected under the reaction conditions. The relatively non-toxic nature of the catalyst, its ease of handling, easy availability and low cost make this procedure especially attractive for large-scale synthesis.
Bismuth Compounds In Organic Synthesis. Synthesis Of Resorcinarenes Using Bismuth Triflate, Ram S. Mohan, Katherine E. Peterson, Russell C. Smith
Dec 2002
Bismuth Compounds In Organic Synthesis. Synthesis Of Resorcinarenes Using Bismuth Triflate, Ram S. Mohan, Katherine E. Peterson, Russell C. Smith
Ram S. Mohan
Bismuth triflate (5 mol%) smoothly catalyzes the condensation of aromatic and aliphatic aldehydes with resorcinol to give tetrameric cyclic products, resorcinarenes. With benzaldehyde, the product is obtained as a mixture of two diastereomers and the ratio of the diastereomers depends on reaction time. On the other hand, a single diastereomer is obtained with aliphatic aldehydes. The low toxicity and ease of handling of bismuth compounds coupled with fast reaction times make this method an attractive alternative to the existing methods for resorcinarene formation
Bismuth Compounds In Organic Synthesis. Deprotection Of Ketoximes Using Bismuth Bromide-Bismuth Triflate, Ram S. Mohan, Joshua N. Arnold, Patrick D. Hayes, Robert L. Kohaus
Dec 2002
Bismuth Compounds In Organic Synthesis. Deprotection Of Ketoximes Using Bismuth Bromide-Bismuth Triflate, Ram S. Mohan, Joshua N. Arnold, Patrick D. Hayes, Robert L. Kohaus
Ram S. Mohan
Ketoximes undergo deprotection in CH3CN/acetone/H2O (3:6:1) in the presence of 20–40 mol% BiBr3/5 mol% Bi(OTf)3. Bismuth(III) salts are relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively non-toxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.
Bismuth Triflate Catalyzed Allylation Of Acetals: A Simple And Mild Method For Synthesis Of Homoallyl Ethers, Ram S. Mohan, Laura C. Wieland, Herbert M. Zerth
Dec 2001
Bismuth Triflate Catalyzed Allylation Of Acetals: A Simple And Mild Method For Synthesis Of Homoallyl Ethers, Ram S. Mohan, Laura C. Wieland, Herbert M. Zerth
Ram S. Mohan
The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis.
Applications Of Bismuth(Iii) Compounds In Organic Synthesis, Ram S. Mohan, Nicholas M. Leonard, Laura C. Wieland
Dec 2001
Applications Of Bismuth(Iii) Compounds In Organic Synthesis, Ram S. Mohan, Nicholas M. Leonard, Laura C. Wieland
Ram S. Mohan
No abstract provided.
The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram S. Mohan, Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday
Dec 2000
The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram S. Mohan, Marcus E. Cabay, Brad J. Ettlie, Adam J. Tuite, Kurt A. Welday
Ram S. Mohan
The E2 elimination is one of the most important reactions in organic chemistry and is discussed in considerable detail in a sophomore organic course. We have developed a discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram S. Mohan, Bryce A. Nattier, Kyle J. Eash
Dec 2000
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram S. Mohan, Bryce A. Nattier, Kyle J. Eash
Ram S. Mohan
Ketoximes undergo facile deprotection in acetone-H20 (9: 1) in the presence 01' 0.5 equivalents of Bi(N03h•5H20. Bismuth(III) nitrate is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively nontoxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.
The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Rebecca S. Centko
Dec 2000
The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Rebecca S. Centko
Ram S. Mohan
Epoxidation of alkenes using peroxyacids is one of the most fundamental reactions in organic chemistry, yet there are very few examples of laboratory experiments that illustrate this important reaction. We have developed a discovery-oriented lab experiment that illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-β-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy. The added element of discovery ensures that students' interest and enthusiasm are retained.
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram S. Mohan, Kaushik A. Bhatia, Kyle J. Eash, Nicholas M. Leonard, Matthew C. Oswald
Dec 2000
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram S. Mohan, Kaushik A. Bhatia, Kyle J. Eash, Nicholas M. Leonard, Matthew C. Oswald
Ram S. Mohan
Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C―O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram S. Mohan, Marc D. Carrigan, Kyle J. Eash, Matthew C. Oswald
Dec 2000
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram S. Mohan, Marc D. Carrigan, Kyle J. Eash, Matthew C. Oswald
Ram S. Mohan
Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3•xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.
The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas
Dec 1999
The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas
Ram S. Mohan
Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate. The identity of the product can be easily determined by 1H NMR spectroscopy and, in case of the trans isomer, by preparation of the semicarbazone derivative as well. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
Isolation Of Curcumin From Tumeric, Ram S. Mohan, Andrew M. Anderson, Matthew S. Mitchell
Dec 1999
Isolation Of Curcumin From Tumeric, Ram S. Mohan, Andrew M. Anderson, Matthew S. Mitchell
Ram S. Mohan
No abstract provided.
Bismuth(Iii) Oxide Perchlorate Promoted Rearrangement Of Epoxides To Aldehydes And Ketones, Ram S. Mohan, Andrew M. Anderson, Jesse M. Blazek, Parie Garg, Brian J. Payne
Dec 1999
Bismuth(Iii) Oxide Perchlorate Promoted Rearrangement Of Epoxides To Aldehydes And Ketones, Ram S. Mohan, Andrew M. Anderson, Jesse M. Blazek, Parie Garg, Brian J. Payne
Ram S. Mohan
Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement in the presence of 10–50 mol% bismuth(III) oxide perchlorate, BiOClO4•xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C―O bond is formed. BiOClO4•xH2O is relatively non-toxic, insensitive to air and inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3•Et2O or InCl3 currently used to effect epoxide rearrangements.
The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick
Jul 1999
The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick
Ram S. Mohan
We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.
The Discovery-Oriented Approach To Organic Chemistry 1. Nitration Of Unknown Organic Compounds. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Sonia R. Mcelveen, Kostas Gavardinas, Jean A. Stamberger
Mar 1999
The Discovery-Oriented Approach To Organic Chemistry 1. Nitration Of Unknown Organic Compounds. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Sonia R. Mcelveen, Kostas Gavardinas, Jean A. Stamberger
Ram S. Mohan
Nitration is one of the most fundamental reactions in organic chemistry. However, the majority of the nitration experiments found in the standard lab textbooks are of the "cookbook" variety and convey none of the excitement associated with discovery in experimental chemistry. We have developed two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. 13 C NMR spectroscopy is a powerful structure elucidation tool and yet not many examples of the use of 13C NMR spectroscopy in organic lab experiments can be found. The experiment involves nitration …
