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The interaction of cis and trans ‐1‐cyclohexyl‐2‐phenyl‐3‐benzoylaziridine with lithium N ‐Methylanilide
Author(s) -
Tarburton Philip,
Wall D. K.,
Cromwell Norman H.
Publication year - 1976
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.5570130246
Subject(s) - chemistry , dehydrogenation , lithium (medication) , benzaldehyde , medicinal chemistry , bond cleavage , stereochemistry , organic chemistry , catalysis , medicine , endocrinology
A reaction pathway for the rearrangement‐dehydrogenation of cis ‐1‐cyclohexyl‐2‐phenyl‐3‐benzoylaziridine into 2‐cyclohexylamino‐3‐phenylindenone can now be suggested. Furthermore, a competing degradation pathway involving CC bond scission accounts for the major product in these reactions and leads to ω‐cyclohexylaminoacetophenone and benzaldehyde. Observed also is the fact that trans ‐1‐cyclohexyl‐2‐phenyl‐3‐benzoylaziridine fails to undergo the rearrangement‐dehydrogenation reaction.