The mechanisms involved in the photosensitized decomposition of methyl diazoacetate (1) were studied by examining the effect of 1 on the CIDNP phenomena observed during the ultraviolet irradiation of benzaldehyde (2) and benzoin (3) in cyclohexane-benzene solutions. The CIDNP spectra generated by photolysis of 3 were not changed significantly by the addition of 1. In contrast, the spectra observed during irradiation of 2 were suppressed by the addition of 1 and replaced by CIDNP signals of products formed by reaction of 1 with 2 or with cyclohexane. These results exclude a chemical sensitization mechanism and therefore support an alternative mechanism, energy transfer from triplet 2 to 1 leading to triplet carbomethoxycarbene.
All Science Journal Classification (ASJC) codes
- Colloid and Surface Chemistry