97250-57-2Relevant academic research and scientific papers
FORMATION OF QUATERNARY CARBON CENTRES FROM TERTIARY ALCOHOLS BY FREE RADICAL METHODS
Barton, Derek H.R.,Crich, David
, p. 757 - 760 (1985)
The deoxygenation of tertiary alcohols via the radical decomposition of their mixed oxalate esters with N-hydroxypyridine-2-thione in the presence of electron deficient olefins leads to the formation of quaternary carbon centres in reasonable yield.
The Invention of New Radical Chain Reactions. Part 11. A New Method for the Generation of Tertiary Radicals from Tertiary Alcohols
Barton, Derek H. R.,Crich, David
, p. 1603 - 1612 (2007/10/02)
A convenient procedure for the radical deoxygenation of tertiary alcohols has been invented using the double half esters of oxalic acid with the t-alcohol and N-hydroxypyridine-2-thione.Decomposition of this type of ester in the presence of 1,1-dimethylethane- or (better) 1,1-diethylpropane-thiol gave the corresponding hydrocarbons in good yield.It has been shown that the oxalate fragmentation is not concerted, but involves a stepwise loss of carbon dioxide.Tertiary alcohols are also a convenient source of radicals for addition to siutable alkenes with formation of quaternary centres.
