Effects of Solvent on the 1,2-Hydrogen Shift to a Divalent Carbon
1974; NRC Research Press; Volume: 52; Issue: 2 Linguagem: Inglês
10.1139/v74-040
ISSN1480-3291
AutoresMichael T. H. Liu, David H. T. Chien,
Tópico(s)Synthesis and Catalytic Reactions
ResumoThe thermal decomposition of 3-chloro and 3-bromo-3-ethyldiazirine in various solvents has been investigated. A comparison was made between the decomposition in gas phase and in solution. The nature of the solvent does not affect the rate of diazirine decomposition, but does alter the subsequent reactions of the carbene. The results show that the cis olefin is predominant in a non-polar solvent but less so in polar solvent. These results were successfully explained by considering the electrostatic interaction of the CH 3 δ+ and Cl δ− groups.
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