Unusual temperature-dependent isotope effects in the reactions of phenylcarbene with cyclohexene and cyclohexane

TG Savino, K Kanakarajan…

Index: Savino, T. G.; Kanakarajan, K.; Platz, M. S. Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1305 - 1309

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Citation Number: 34

Abstract

The photochemistry of phenyldiazomethane in cyclohexene (cyclohexene-d,,) and cyclohexane (cyclohexane-d12) was studied. The chemistry observed was found to be entirely consistent with singlet rather than triplet phenylcarbene reactions. Small (1.9-2.1) isotope effects to CH insertion were observed at 25" C that increased on cooling. Cooling to very low temperature (-196 OC) reduced the isotope effect. The results are discussed in ...

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