Benzocyclobutenylidene-cycloadditions, reactivity, and multiplicity

…, H Nickels, LA Pacala, M Jones Jr

Index: Duerr, Heinz; Nickels, Helmut; Pacala, Luba A.; Jones, Maitland Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 973 - 980

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Citation Number: 42

Abstract

EHT and CNDO/2 calculations on benzocyclobutenylidene (6) are described. Flash pyrolysis of the tosylhydrazone salt 7 affords benzocyclobutene and o-xylene in low yield, along with the formal syn and anti carbene dimers 13 and 14. Condensed-phase reactions were achieved by photolysis of the salt 15. Benzocyclobutenylidene (6) gave rise to the formal carbene dimers 17 and 18. Insertion of carbene 6 into the carbon-hydrogen bonds ...