The Journal of Organic Chemistry

Out-of-Ring Claisen Rearrangements1

A Nickon, BR Aaronoff

Index: Nickon,A.; Aaronoff,B.R. Journal of Organic Chemistry, 1964 , vol. 29, p. 3014 - 3021

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Citation Number: 11

Abstract

The objective was to investigate Claisen rearrangements of allyl groups to carbons that are located outside the parent phenol ring. Pyrolysis of the allyl ether (7) of 2, 6-dimethyl- 4propenylphenol (6) in ethanol at 200" followed by catalytic hydrogenation gave 2, 6- dimethyl-4-propylphenol (9, 8.57,) and 2, 6-dimethyl-4 (2-methylpenty1) phenol (12, 32%). The formation of 12 from 7 is explicable by a sequence of three consecutive cyclic ...