Journal
JOURNAL OF PHYSICAL CHEMISTRY A
Volume 111, Issue 46, Pages 11814-11817Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jp073917u
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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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