81650-75-1Relevant academic research and scientific papers
Experimental and Theoretical Investigation on the Cycloadditions of Nitrile Oxides, Nitrones, and Diazoalkanes with Acyclic Vinyl Sulphones and Thiet 1,1-Dioxide
Benedetti, Pier G. De,Quartieri, Simona,Rastelli, Augusto,Amici, Marco De,Micheli, Carlo De,et al.
, p. 95 - 100 (2007/10/02)
Diazoalkanes, nitrile oxides, and nitrones cycloadd thiet 1,1-dioxide showing regiochemical characteristics markedly different from those observed for acyclic vinyl sulphones.The charge-transfer stabilization energy, calculated according to the Klopman-Salem pertubational approach in the CNDO/2 approximation, is able to account for the experimantal trends of the isomer ratios.An analysis of the calculations performed for cis-syn-vinyl sulphones explains the change of regiochemistry in the reactions of thiet 1,1-dioxide as due to its blocked cis-syn-structure which does not happen in the 'open' vinyl sulphones.Unsuccessful predictions obtained with the frontier orbital approximation are discussed.
