253161-04-5Relevant academic research and scientific papers
Inter- and intramolecular pathways for the formation of tetrahydrofurans from β-(phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism
Crich, David,Huang, Xianhai,Newcomb, Martin
, p. 523 - 529 (2007/10/03)
β-(Phosphatoxy)alkyl radicals generated by photolysis of Barton PTOC esters in the presence of allyl alcohol and tert-butyl mercaptan undergo nucleophilic substitution followed by 5-exo-trig radical ring closure leading to tetrahydrofurans in good yield and with high trans selectivity. β- (Phosphatoxy)alkyl radicals obtained by intramolecular hydrogen 1,5- abstraction with an alkoxyl radical undergo nucleophilic displacement providing tetrahydrofurans. The ensemble of results, including the effects of leaving groups and substituents, strongly support a dissociative mechanism for these radical nucleophilic displacement reactions.
β-Phosphatoxyalkyl Radical Reactions: Competing Phosphate Migration and Phosphoric Acid Elimination from a Radical Cation - Phosphate Anion Pair Formed by Heterolytic Fragmentation
Newcomb, Martin,Horner, John H.,Whitted, Patrick O.,Crich, David,Huang, Xianhai,Yao, Qingwei,Zipse, Hendrik
, p. 10685 - 10694 (2007/10/03)
β-Phosphatoxyalkyl radical reactions were studied experimentally and computationally. The 1,1-dibenzl-2-(diphenylphosphatoxy)-2-phenylethyl radical (1) reacted to give the migration product 2-benzyl-2-(diphenylphosphatoxy)-1,3-diphenylpropyl radical (2) a
