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Direct Observation of a Photoinduced Nonstabilized Nitrile Imine Structure in the Solid State

2009; American Chemical Society; Volume: 131; Issue: 50 Linguagem: Inglês

10.1021/ja9094523

1943-2984

Shao‐Liang Zheng, Yi‐Zhong Wang, Zhipeng Yu, Qing Lin, Philip Coppens,

Synthesis of Tetrazole Derivatives

We report the direct observation of a bent geometry for a nonstabilized nitrile imine in a metal-coordination crystal. The photoinduced tetrazole ring rupture to release N2 appears to depend on the size of voids around the N3−N4 bond in the crystal lattice. We further observed the selective formation of the 1,3-addition product when a reactive nitrile imine was photogenerated in water. Overall, the bent nitrile imine geometry agrees with the 1,3-dipolar structure, a transient reactive species that mediates the photoinduced 1,3-dipolar cycloaddition in the aqueous medium.