131190-22-2Relevant academic research and scientific papers
ORGANOTIN HOMOENOLATE EQUIVALENTS - ACCESS TO β-ACYL- AND β-ARYL-PROPIONALDEHYDES THROUGH HETEROSUBSTITUTED ALLYLTINS AND VINYLTINS
Verlhac, Jean-Baptiste,Pereyre, Michel,Quintard, Jean-Paul
, p. 6399 - 6412 (2007/10/02)
Although, α-ethoxycrotyltributyltin can be used as an equivalent of the homoenolate anion CH3-CHCH2CHO in reactions with acyl chlorides, the non-substituted α-ethoxyallyltributyltin could not be employed in this way. γ-Methoxyvinyltins, easily prepared by hydrostannation of propargylic ethers, are successfully employed as synthetic equivalents of the homoenolate anions -CH2CH2CHO and -CH2CH2COCH3 in reactions with acyl chlorides.A silylated γ-methoxyvinyltin, which is both a vinyltin and an allylsilane, reacts with acyl chlorides and aryl bromides as a promising equivalent of the homoenolate anion -CH2CH2CHO and tolerates a wide range of other reactive functional groups.
