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A dynamic NMR study of Z, E-isomerization in solutions of indolyl-substituted α-nitroacrylates

✍ Scribed by V. I. Bakhmutov; V. A. Burmistrov; K. K. Babievsky; K. A. Kochetkov; B. A. Kvasov; V. M. Belikov; E. I. Fedin

Publisher: John Wiley and Sons
Year: 1978
Tongue: English
Weight: 352 KB
Volume: 11
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270110609

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✦ Synopsis

Abstract

Fast Z, E‐isomerization of α‐nitro‐β‐indolylacrylates in polar solvents has been studied by dynamic ^1^H NMR spectroscopy. With indolylnitroacrylates having no substituents at the ring nitrogen atom, isomerization proceeds via intermediate formation of a mesomeric anion and ionization of the N–H bond as the rate determining step. For methyl‐substituted indolylnitroacrylates, no general isomerization mechanism can be suggested, and isomerization pathways depend on the structures of isomerizing species.

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