On the deceptive behavior of tri-n-butyltin hydride: In the reduction of acetates of some bromohydrins. A stereospecific radical rearrangement
1986; Elsevier BV; Volume: 27; Issue: 13 Linguagem: Inglês
10.1016/s0040-4039(00)84300-2
ISSN1873-3581
AutoresPavel Kocovsk�, Ivo Starý, František Tureček,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoRadical hydrogenolysis of the bromohydrin acetate 7 with Bu3SnH surprisingly leads to the 6α-acetoxy derivative 8 and not to the expected product 6. Structural requirements of this stereospecific rearrangement are discussed. Isotopic labeling demonstrated that the rearrangement proceeds as a 1,2-shift involving the ether oxygen of the acetoxy group (21 → 22) in contrast to an earlier observation.
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