Dealkylation of a tertiary amine group by an intramolecular carbamyl chloride functionality

…, CA Maryanoff, GP Wooden, RA Olofson

Index: Maryanoff, Bruce E.; Molinari, Albert J.; McComsey, David F.; Maryanoff, Cynthia A.; Wooden, Gary P.; Olofson, R. A. Journal of Organic Chemistry, 1983 , vol. 48, p. 5074 - 5080

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Citation Number: 6

Abstract

R'r R, & R1= R4= H; R2= C6H5; RJ=(CH2) 2C1 rearrangement of 6a. 3 In that communication, we suggested that the facility of the rearrangement (t112= 2.3 h at 23" C) may be attributable to the expected high population of cis-fused conformer in 6a. To test this point and to extend the scope of this uncommon rearrangement, we have investigated the COC12/CF3CH2NH2 reaction with two diastereomers of 4a, anilines 4b and 4c, and with ...