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Nitrene insertion reactions. Part III. The steric effect of the Iso propyl and t ‐butyl groups. 1,6 Type cycloaddition of tetracyanoethylene to 1 H ‐azepines
Author(s) -
Photis James M.
Publication year - 1971
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.5570080508
Subject(s) - chemistry , tetracyanoethylene , azepine , steric effects , nitrene , yield (engineering) , medicinal chemistry , alkyl , cycloaddition , aryl , selectivity , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Various alkyl and aryl carboxynitrenes generated thermally from the azidoformates react with para ‐di‐ t ‐butylbenzene with a high degree of selectivity to yield predominantly, or exclusively, 3,6‐di‐ t ‐butylazepine‐ N ‐carboxylates. 3,6‐Dialkylazepines react readily with tetracyanoethylene to afford the first known TCNR‐1 H ‐azepine cycloadducts of the 1,6 type.