92822-54-3

Upstream product

• 768-95-6 1-adamanthanol 
• 3811-73-2 2-mercaptopyridine-1-oxide sodium salt 
• 92822-43-0 ethyl 2-methylene-3-t-butylthiopropanoate 
• 35389-22-1 2-oxo-2-(adamantan-1-yloxy)acetic acid 
• 768-93-4 1-iodoadamantane 
• 89295-32-9 2-(ethoxycarbonyl)prop-2-en-1-yl phenyl sulfone 
• 2094-72-6 1-Adamantanecarbonyl chloride 

Relevant academic research and scientific papers

Tris(trimethylsilyl)silane as mediator in the radical-based allylation reactions of allyl and 2-functionalized allyl phenyl sulfones

Radical allylations with 2-functionalized allyl phenyl sulfones have been performed by using tris(trimethylsilyl)silane as radical mediator. Yields varied from moderate to good depending on the nature of the starting materials. EPR studies on the alkyl radical adducts of allyl sulfones have been performed and conformational information has been obtained for the tert-butyl and tetrahydrofuranyl adducts of 2-carboxy allyl tris(trimethylsilyl)silane.

The Invention of New Radical Chain Reactions. Part 12. Improved Methods for the Addition of Carbon Radicals to Substituted Allylic Groups

Reagents for the allylation of carbon radicals derived from the esters (mixed anhydrides) of N-hydroxy-2-thiopyridone have been investigated.Because of competition between the background reaction of decarboxylative rearrangement and the desired allylation process, conventional allylation reagents give moderate yields of the desired adducts.Improved yields are secured if the β-position bears an electron withdrawing group.A concerted addition and elimination process can be postulated.

The Invention of New Radical Chain Reactions. Part 11. A New Method for the Generation of Tertiary Radicals from Tertiary Alcohols

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.

FORMATION OF QUATERNARY CARBON CENTRES FROM TERTIARY ALCOHOLS BY FREE RADICAL METHODS

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.

CARBETHOXYALLYLATION USING RADICAL CHEMISTRY

Radicals derived from the esters of N-hydroxy-2-thiopyridone react smoothly in a concerted reaction with 2-carbethoxy-3-t-butylthioprop-1-ene to give the corresponding 2-carbethoxyallyl derivatives with shift of the double bond.