Engineering reactions in crystalline solids: prediction of intramolecular carbene rearrangements

MA Garcia-Garibay, S Shin, CN Sanrame

Index: Garcia-Garibay, Miguel A; Shin, Steve; Sanrame, Carlos N Tetrahedron, 2000 , vol. 56, # 36 p. 6729 - 6737

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Citation Number: 32

Abstract

The unimolecular reactivity and stereoselectivity of four arylalkyl carbenes generated by a steady state irradiation of crystalline 1, 2-diaryldiazopropanes were correctly predicted by taking advantage of known reaction trajectories applied to structures obtained by simple molecular mechanics calculations. It is suggested that the conformation of the diazo compound in the crystal determines the conformation of the carbene intermediate which is ...