Et3B versus AIBN: Equally radical? The stereoselectivity of hydrostannylation of internal propargyl alcohol derivatives has been studied by using both 2-2′-azobisisobutyronitrile (AIBN) and Et3B as promoters. With silyl-protected alcohols, complete Z selectivity of the resultant vinylstannane has been achieved with Et3B, whereas AIBN shows zero stereoselectivity. Evidence suggests that, despite decades of acceptance, the hydrostannylation mechanisms employing Et3B and AIBN appear to be mechanistically distinct.
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