Reactivity of iso-diiodomethane and iso-iodoform, isomers of CH2I2 and CHI3, toward the double bond of a variety of cycloalkenes |
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| Authors: | Tarnovsky Alexander N Pascher Irmin Pascher Torbjörn |
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| Institution: | Department of Chemistry and Center for Photochemical Sciences, Bowling Green State University, Bowling Green, Ohio 43403, USA. atarnov@bgsu.edu |
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| Abstract: | The metastable CH2I-I and CHI2-I isomers formed by UV photolysis of CH2I2 and CHI3 transfer methylene and iodomethylene groups, respectively, to a variety of cycloalkenes, leading to their cyclopropanation. More than a 100-fold increase of the reaction rate with increasing solvent polarity suggests a dipolar transition state. The fastest second-order rates observed were in CH3CN. However, CH2Cl2 will be the more appropriate reaction medium because the isomer thermal stability is greater in CH2Cl2 than in the more polar CH3CN. |
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