Synthesis of ethylenes with acyclic quaternary carbons by dehydration of neopentyl alcohols. Application of the 2-D INAPT technique

CA Drake, N Rabjohn, MS Tempesta…

Index: Drake, C. A.; Rabjohn, Norman; Tempesta, Michael S.; Taylor, Richard B. Journal of Organic Chemistry, 1988 , vol. 53, # 19 p. 4555 - 4562

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Citation Number: 12

Abstract

Di-and triquaternary ethylenes (5, 12 and 7, 19, Scheme I) have been synthesized by dehydration of sec-and tert-neopentyl alcohols (4, 11 and 6, 18) without rearrangement. It is thought that steric factors determine the structures of the products. The intermediate imines 2 and 14, from the reaction of nitriles 1 and 13 with tC, H&i, may be hydrolyzed only in the first case to ketones (3). More highly substituted ketones (10 and 16) were obhned by the ...