DECOMPOSITION OF TOSYLHYDRAZONES OF BENZOIN, BENZOIN ACETATE, AND BENZOIN BENZOATE WITH ALKALI AND METAL-COMPLEX HYDRIDES

Authors
IWADARE T ICHINOHE Y ORITO K
Citation
T. Iwadare et al., DECOMPOSITION OF TOSYLHYDRAZONES OF BENZOIN, BENZOIN ACETATE, AND BENZOIN BENZOATE WITH ALKALI AND METAL-COMPLEX HYDRIDES, Canadian journal of chemistry, 74(2), 1996, pp. 227-231
Citations number
24
Categorie Soggetti
Chemistry
Journal title
Canadian journal of chemistry → ACNP
ISSN journal
00084042
Volume
74
Issue
2
Year of publication
1996
Pages
227 - 231
Database
ISI
SICI code
0008-4042(1996)74:2<227:DOTOBB>2.0.ZU;2-L
Abstract
Treatment of tosylhydrazones of benzoin, benzoin acetate, and benzoin benzoate with alkali under protic and aprotic conditions yielded diphe nyl acetylene together with desoxybenzoin. An increase in leaving apti tude of the adjacent group enhanced the formation of diphenyl acetylen e. By treatment with LiAlH4 and with NaBH4, the tosylhydrazones gave s tilbenes in good yields. Selective formation of cis- or trans-stilbene was observed in some cases.