… for using alkoxide-accelerated vinylcyclobutane ring expansions in the synthesis of six-membered rings. Unexpected orbital symmetry allowed and forbidden 1, 3- …

T Cohen, M Bhupathy, JR Matz

Index: Cohen; Bhupathy; Matz Journal of the American Chemical Society, 1983 , vol. 105, # 3 p. 520 - 525

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Citation Number: 44

Abstract

Abstract: A practical method for utilizing the ring expansion of 2-vinylcyclobutanols to cyclohex-3-en-l-ols, even in cases in which very acid-sensitive groups are present, consists of the addition of 1-lithio-1-methoxycyclopropanes to conjugated enals, brief treatment in the cold of the resulting alcohols with dilute acid, conversion of the resulting 2- vinylcyclobutanones to the corresponding alcohols, and treatment of the latter with ...