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1,3‐Dipolare Cycloadditionen von Nitrilium‐Betainen mit 4,4‐Dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thion
Author(s) -
Büchel Thomas,
Prewo Roland,
Bieri Jost H.,
Heimgartner Heinz
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670222
Subject(s) - chemistry , benzonitrile , cycloaddition , ylide , medicinal chemistry , azomethine ylide , double bond , nitrile , 1,3 dipolar cycloaddition , stereochemistry , organic chemistry , catalysis
1,3‐Dipolar cycloadditions of Nitrilium Betaines with 4,4‐Dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thione Benzonitrile ylides, imines, and oxides undergo smooth 1,3‐dipolar cycloaddition reactions with the exocyclic, C,S‐double bond of 4,4‐dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thione ( 1 ), yielding heterocyclic spiro‐compounds. The structure of the cycloadducts 5c, 5c ′, and 3f ( Fig. ) have been established by x‐ray structure analysis. With the benzonitrile ylides, the two regioisomeric cycloaddition modes have been observed, depending on the substituents of the ylide‐C‐atom. It is questionable, whether the reaction of 1 and the oxazaphosphol 8 ( Schemes 8 and 13 ) proceeds via the corresponding nitrile ylide as an intermediate.