THE INVENTION OF RADICAL REACTIONS .32. RADICAL DEOXYGENATIONS, DEHALOGENATIONS, AND DEAMINATIONS WITH DIALKYL PHOSPHITES AND HYPOPHOSPHOROUS ACID AS HYDROGEN SOURCES

Citation
Dhr. Barton et al., THE INVENTION OF RADICAL REACTIONS .32. RADICAL DEOXYGENATIONS, DEHALOGENATIONS, AND DEAMINATIONS WITH DIALKYL PHOSPHITES AND HYPOPHOSPHOROUS ACID AS HYDROGEN SOURCES, Journal of organic chemistry, 58(24), 1993, pp. 6838-6842
Citations number
88
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
58
Issue
24
Year of publication
1993
Pages
6838 - 6842
Database
ISI
SICI code
0022-3263(1993)58:24<6838:TIORR.>2.0.ZU;2-I
Abstract
Reagents, containing a P-H bond, such as dimethyl phosphite, diethyl p hosphite, hypophosphorous acid and various salts of hypophosphorous ac id are effective radical reducing agents for organic halides, thionoes ters, and isocyanides affording high yields of the corresponding hydro carbons. Reduction of tertiary phenyl selenides and tertiary nitro com pounds are not efficient under these conditions. Olefination of 1,2-di ols is also accomplished via the corresponding thiocarbonyl derivative s using hypophosphorous acid and triethylamine in the presence of a su itable ''sacrificial olefin'' in moderate to good yields.