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