Benzonorbornene and derivatives. IV. Bridgehead and 1-carbinyl derivatives

JW Wilt, HF Dabek Jr, JP Berliner…

Index: Wilt,J.W. et al. Journal of Organic Chemistry, 1970 , vol. 35, # 7 p. 2402 - 2410

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Citation Number: 5

Abstract

Benzonorbornenyl-1-carbinyl tosylate (1) is investigated as a possible model for a non-? r- participatory neophyl system. Its solvolysis compared with that of the nonbenzo analog 9 is retarded 47-fold in acetic acid at 133'and 14-fold in 80% acetone at 25'. No evidence for anchimeric assistance by the aromatic ring was found. Under the vigorous conditions of refluxing hydrobromic acid containing zinc bromide, benzonorbornenyl-lcarbinol (8) still ...