Neighboring-Group participation in the gas phase. Loss of benzaldehyde from [(benzyloxy)methyl]dialkylsilyl-substituted 1,3-dithianes

摘要: [(Benzyloxy)methyl]dialkylsilyl-substituted 1,3-dithianes show in CI-MS an abundant loss of benzaldehyde from the [M + H]+ quasi-molecular ion. The fragmentation is explained with intramolecular redox process, where a hydride proposed to be transferred benzyl position neighboring thionium This would form particle that could readily lose as neutral fragment. results provide explanation for unusual instability (benzyloxy)methyl-substituted silanes towards acids. In fact, formation was established decomposition acylsilane presence Lewis or Bronsted acids and ethanethiol. study, therefore, represents useful method recognize reactions are – might important solution.