Experimental and theoretical investigations of ring-expansion in 1-methylcyclopropylcarbene

…, JR Snoonian, HM Sulzbach, CM Hadad

Index: Thamattoor, Dasan M.; Snoonian, John R.; Sulzbach, Horst M.; Hadad, Christopher M. Journal of Organic Chemistry, 1999 , vol. 64, # 16 p. 5886 - 5895

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Citation Number: 21

Abstract

1-Methylcyclopropylcarbene, generated by photolysis of two isomeric hydrocarbon precursors, undergoes ring-expansion readily to give 1-methylcyclobutene. Experimentally, intramolecular carbon-hydrogen insertions are not observed. Trapping studies with TME demonstrates the formation of the expected cyclopropane adduct, and via a double- reciprocal analysis, the lifetime of 1-methylcyclopropylcarbene was determined to be 12 ...