ON THE REACTION OF THIOCHROMAN-4-ONE AND 3-(HYDROXYMETHYLENE)THIOCHROMAN-4-ONE WITH N-CHLOROSUCCINIMIDE

Treatment of 3-(hydroxymethylene)thiochroman-4-one (4) with N-chlorosuccinimide afforded efficient routes to 3-chlorothiochroman-4-one (5), 3-chlorothiochromone (6) and 2,3-dichlorothiochromone (7). Contrary to an earlier report, 3-formylthiochromone was not obtained from this reaction. The products...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 45; no. 2; pp. 439 - 443
Main Authors GILES, PR, MARSON, CM
Format Journal Article
LanguageEnglish
Published COLLINGWOOD C S I R O PUBLICATIONS 01.01.1992
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:Treatment of 3-(hydroxymethylene)thiochroman-4-one (4) with N-chlorosuccinimide afforded efficient routes to 3-chlorothiochroman-4-one (5), 3-chlorothiochromone (6) and 2,3-dichlorothiochromone (7). Contrary to an earlier report, 3-formylthiochromone was not obtained from this reaction. The products obtained are rationalized in terms of C-chlorination, in contrast to the action of N-chlorosuccinimide on thiochroman-4-one (1), for which S-chlorination is postulated.
ISSN:0004-9425
DOI:10.1071/CH9920439