Premium
Nitrene insertion reactions. 1. Dimethyl N ‐carbethoxyazepines and their cycloaddition reaction products
Author(s) -
Photis James M.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070604
Subject(s) - chemistry , tetracyanoethylene , cycloaddition , nitrene , adduct , medicinal chemistry , nitroso , benzene , photochemistry , nitroso compounds , organic chemistry , catalysis
Dimethyl‐ N ‐carbethoxyazepines, isolated from the reaction between ethyl azidoformate and o ‐, m ‐ and p ‐xylenes, react with tetracyanoethylene to give [4 + 2] Diels‐Alder adducts. Nitroso‐benzene is inert toward 2‐methylazepines, but reacts with 3,6‐dimethyl‐ N ‐carbethoxyazepine to give a [6 + 2] cycloadduct. The effect of two methyl substituents on the course of the cycloaddition reactions is discussed.