Reaction of 2-(. DELTA. 3-cyclopentenyl) ethyl bromide with tri-n-butyltin hydride. Cyclization to norbornane

JW Wilt, SN Massie, RB Dabek

Index: Wilt,J.W. et al. Journal of Organic Chemistry, 1970 , vol. 35, # 8 p. 2803 - 2806

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Citation Number: 29

Abstract

The reduction of 2-(A3-cyclopentenyl) ethyl bromide (1) with tri-n-butyltin hydride proceeds with some cyclization to norbornane (3). The cyclization process is discussed in terms of purportedly delocalized intermediates in the analogous cationic process. The conclusion is reached that successful cyclization of 2-(A3-cyc1opentenyl) ethyl substrates does not necessarily indicate delocalized intermediates. Rather, a favorable geometry in the ...