1, 2, 4, 6-Cycloheptatetraene: the key intermediate in arylcarbene interconversions and related C7H6 rearrangements

RJ McMahon, CJ Abelt, OL Chapman…

Index: McMahon, Robert J.; Abelt, Christopher J.; Chapman, Orville L.; Johnson, Jeffery W.; Kreil, Curits L.; et al. Journal of the American Chemical Society, 1987 , vol. 109, # 8 p. 2456 - 2469

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Citation Number: 117

Abstract

Abstract: Thermolysis or photolysis of phenyldiazomethane (2) produces phenylmethylene (3), which ring-expands to give 1, 2, 4, 6-~ ycloheptatetraene (6). Spectroscopic and chemical evidence rule out bicyclo [4.1. O] hepta-2, 4, 6-triene (4), cycloheptatrienylidene (S), and bicyclo [3.2. 0] hepta-1, 3, 6-triene (11) intermediates. The strained allene in cycloheptatetraene (6) exhibits infrared absorptions at 1824 and 1816 cm-l. Deuterium ...