Tetrahedron Letters

Cyclopentenone and cyclohexenone annulations via acid-catalyzed 1, 2-and 1, 3-acyl migration of 2-vinylcyclobutanones. Rearrangement route to spiro-and …

JR Matz, T Cohen

Index: Matz, James R.; Cohen, Theodore Tetrahedron Letters, 1981 , vol. 22, # 26 p. 2459 - 2462

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Citation Number: 30

Abstract

Abstract In the presence of acid, 2-alkyl-2-vinylcyclobutanones rearrange mainly by a 1, 2- acyl migration to give cyclopentenones while 2-vinylcyclobutanones lacking 2-alkyl substituents undergo a 1, 3-acyl migration to produce cyclohexenones; the former rearrangement can be used to produce angularly substituted fused bicyclic systems.

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