Cyclopropanol Derivatives as Intermediates for Organochemical Synthesis

Abstract

A design of terpene synthesis based on the acid-induced transformations of cyclopropyl ethers and β-methoxycyclopropylcarbinols into quaternary α-methyl and α-vinyl carbonyl compounds, respectively, is described. Similar reactions with gem-dimethoxycyclopropanes are portrayed. A cyclopropylamine is shown to be inert. β-Methoxycyclopropanecarboxylic esters are converted into γ-ketocarboxylic acid derivatives. A similar ring unravelling of a β-acetoxycyclopropyl ketone is used for the synthesis of dihydrojasmone. An α-methoxycyclopropylcarbinol is transformed into a cyclobutanone on acid treatment and a mechanistically related cyclobutanone interconversion process is utilized for the construction of a bicyclic intermediate on route to the bourbonene sesquiterpenes. © 1970, American Chemical Society. All rights reserved.