Origin of the". beta.-Oxygen Effect" in the Barton Deoxygenation Reaction

…, L Quintero-Cortes, J Sandoval-Ramirez

Index: Crich, David; Beckwith, Athelstan L. J.; Chen, Chen; Yao, Qingwei; Davison, Ian G. E.; Longmore, Robert W.; De Parrodi, Cecilia Anaya; Quintero-Cortes, Leticia; Sandoval-Ramirez, Jesus Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8757 - 8768

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Citation Number: 50

Abstract

Abstract: Photolysis of 0-neopentyl S-tributylstannyl dithiocarbonate with hexaphenyl distannane, and 4-methoxyacetophenone as sensitizer, results in crossover of the stannyl groups. The reaction of 0-octyl 0'-(2-butoxyethyl) thiocarbonate with tributyltin deuteride or tns (trimethy1silyl) silane and a radical initiator shows no significant preference for the cleavage of either C-0 bond. Intermolecular competitions between 0-octyl O'-phenyI ...