Reactions with aziridines, 46. Ring opening of stilbene imines by thiophenolate | Zendy

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Reactions with aziridines, 46. Ring opening of stilbene imines by thiophenolate

Author(s) -

Mall Thomas,

Stamm Helmut

Publication year - 1988

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19881210722

Subject(s) - chemistry , diastereomer , aziridine , protonation , ring (chemistry) , stereochemistry , bicyclic molecule , medicinal chemistry , organic chemistry , ion

Ring opening by thiophenolate of cis ‐ trans pairs of stilbene imines proceeds stereospecifically irrespective of the kind of mono activation by the phenylsulfonyl group ( 1 ), by the benzoyl group ( 2 ), or by protonation of the aziridine base ( 3 ). In accordance with complete Walden inversion, the sole product from the cis isomer is always a diastereomer of the sole product from the trans isomer. The diastereomers obtained from 3 are correlated with the respective diastereomers obtained from 2 .

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