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- W2000776731 abstract "The brosylates of ..cap alpha..,..cap alpha..-/sup 2/H/sub 2/-, ..beta..,..beta..-/sup 2/H/sub 2/-, and ..cap alpha..,..cap alpha..,..beta..,..beta..-/sup 2/H/sub 4/-..beta..-(syn-7-norbornenyl)ethanol have been prepared and solvolyzed at 25/sup 0/C in buffered acetic acid, in buffered formic acid, and in buffered 90 percent acetone-water. The deuterated exo-2-brendyl and exo-4-brexyl derivatives produced in each case after a single hydrogen or deuterium shift have been converted to deuterated brendan-2-one and brexan-4-one mixtures and the position of the deuterium labels in each ketone determined mass spectrometrically. Comparison of the deuterium content of the brexan-4-one both before and after base-catalyzed exchange with protium permits analysis of the fractions of solvolysis product derived from each recognizably discrete rearranged cation. From these results it is clear that some hydrogen or deuterium migration occurs from each methylenic carbon of the starting brosylate and that 10 to 19 percent of those migrations are preceded by at least one Wagner--Meerwein automerization. It is suggested that the observed effect of the different solvents on the product distribution is due in part to ion pairing which affects the rate of transformations that change the net charge separation in the initial intermediate." @default.
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- W2000776731 date "1977-01-01" @default.
- W2000776731 modified "2023-10-18" @default.
- W2000776731 title "Solvolysis of deuterium-labeled .beta.-(syn-7-norbornenyl)ethyl p-bromobenzenesulfonates. Multiple cation automerizations in tight ion pairs" @default.
- W2000776731 doi "https://doi.org/10.1021/ja00443a036" @default.
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