Through-bond interaction via cyclobutane relay orbitals as a means of extending conjugation. Synthesis of tricyclo [5.5. 0.02, 8] dodecatetraene, tricyclo [5.3. 0.02, 8] …

J Dressel, KL Chasey, LA Paquette

Index: Dressel,J.; Chasey,K.L.; Paquette,L.A. Journal of the American Chemical Society, 1988 , vol. 110, p. 5479

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Citation Number: 17

Abstract

Abstract: The title hydrocarbons have been prepared from dimethyl e-truxillate. Stepwise belting of a preformed all-trans 1, 2, 3, 4-tetrasubstituted cyclobutane with proper differentiation of the 1, 3-and 2, 4-positions permits the necessary twofold annulation to be accomplished with relative ease. The efficiency of the syntheses has made available quantities of 8-10 sufficiently large for physicochemical study.