Journal of the American Chemical Society

Mechanistic and synthetic applications of silver (I)-promoted alkoxyl group ionization processes. Evaluation of cyclopropylcarbinyl and benzhydryl ethers

G Zon, LA Paquette

Index: Zon,G.; Paquette,L.A. Journal of the American Chemical Society, 1974 , vol. 96, p. 5478 - 5487

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Citation Number: 3

Abstract

Abstract: The reaction of a number of endo-2-methoxytricycIo [4.1. 0.03, 7] heptanes with silver perchlorate in benzene at 40” leads to quantitative isomerization to anti-7- methoxynorbornenes by a process involving initial Ag+.*. OR (CH3) coordination, methoxyl group ionization, and recapture of the alkoxide after cyclopropylcarbinyl-+ homoallyl rearrangement. Several norcaranyl ethers were examined under comparable conditions; ...

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