65094-89-5Relevant academic research and scientific papers
One-pot synthesis of epoxides from benzyl alcohols and aldehydes
Alfonzo, Edwin,Mendoza, Jesse W.L.,Beeler, Aaron B.
, p. 2308 - 2312 (2018/09/14)
A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.
Enantioconvergent transformation of racemic cis-β-alkyl substituted styrene oxides to (R,R) threo diols by microsomal epoxide hydrolase catalysed hydrolysis
Bellucci, Giuseppe,Chiappe, Cinzia,Cordoni, Antonio
, p. 197 - 202 (2007/10/03)
Both enantiomers of cis-β-ethyl, β-n-propyl, β-n-butyl, and β-n-hexyl substituted styrene oxides undergo microsomal epoxide hydrolase catalysed hydration at the (S) carbon to give the corresponding (R, R) threo diols in a > 90% e.e. A complete kinetic resolution of the racemic epoxide is also obtained with the β-ethyl substituted substrate, but not with its higher homologues.
On the conformational preferences of the dehydrochlorination of α-chlorosulfoxides
Schwan, Adrian L.,Roche, Michael R.,Gallagher, John F.,Ferguson, George
, p. 312 - 324 (2007/10/02)
Several acyclic α-chlorosulfoxides have been shown to undergo a γ-dehydrochlorination upon treatment with LDA.The proposed immediate products of γ-dehydrochlorination, thiirane-S-oxides, are unstable under the basic conditions and react further with the LDA; the isolated products are usually E-alkenes and (or) E-vinyl sulfoxides.Some of the proposed intermediate thiirane-S-oxides, compounds 6, 7, 8, and 18, were synthesized independently and treated with one equivalent of LDA in order to mimic the second step of the overall dehydrochlorination/ring opening sequence.The products obtained from the reactions of compounds 6 and 18 compared favourably with those products which were believed to arise from certain conformations of α-chlorosulfoxides 1kB and 1e, respectively.Tha addition of one equivalent of LDA to 1kA afforded a mixture containing thiirane-S-oxide 8, which is proposed as the immediate product of γ-dehydrochlorination of 1kA.The configurations of 1kB and 1hA were both shown to be threo by X-ray crystallographic studies.Those conformations which are preferred for the dehydrochlorination possess a geometry where the sulfinyl oxygen is anti to any of the substituents of the ring carbons.
Photolysis and Thermolysis of 3-n-Butyl-3-phenyldiazirine
Liu, Michael T. H.,Palmer, Glenn E.,Chishti, Najmul H.
, p. 53 - 57 (2007/10/02)
The photochemical and thermal decompositions of 3 butyl-3-phenyldiazirine have been investigated in acetic acid and acetic acid, and in other solvents with and without m-chloroperbenzoic acid.The results are consistent with the fact that the oxidation products are derived mainly from the reactions of 1-diazo-1-phenylpentane.
