267417-97-0Relevant academic research and scientific papers
Substituent effects on the stereochemical course of electrophile- initiated tetrahydropyran-forming reactions: A possible stereoelectronic effect
Hart, David J.,Patterson, Suzanne,Zakarian, Alain
, p. 1025 - 1028 (2007/10/03)
A series of 4-penten-1,3-diol derivatives were prepared and treated with phenylselenenyl chloride to provide tetrahydropyrans. The stereochemical course of the reactions is consistent with a chair-like transition state in which the oxygen substituent at the 3-position largely occupies an axial site. A structurally related 3-methyl-4-penten-1-ol derivative gave a major product consistent with a chair transition state in which the methyl group occupies an equatorial site.
