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The role of solvent in conjugate additions leading to cis and trans ‐1‐Alkyl‐2‐aryl‐3‐carbo(aroyl)aziridines
Author(s) -
Tarburton Phillip,
Woller Paul B.,
Badger Robert C.,
Doomes Earl,
Cromwell Norman H.
Publication year - 1977
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.5570140321
Subject(s) - chemistry , alkyl , amine gas treating , solvent , aryl , conjugate , halogen , medicinal chemistry , primary (astronomy) , enol , solvent effects , benzene , organic chemistry , catalysis , mathematical analysis , physics , mathematics , astronomy
In the formation of cis ‐ and trarn ‐1‐alkyl‐2‐aryl‐3‐carbo(aroyl)aziridines a change in solvent from benzene to rnethanol in the α‐bromochalone‐primary amine reaction produced an increase in cic isotner. However, the same solvent change resulted in a decrease in the cis/trans ratio when these same aziridines were prepared by the ehalcone‐halogen‐primary amine reaction. These results are rationalized in terms of both an open and chelated enol intermediate thought to be crucial in the relative product formations. Other mechanistic considerations in the product formations are presented.