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X-ray Structures of Cyclophanes Derived from Naphtho 1,2-c:5,6-c -difuran and the Synthesis, Structure, and Reaction Kinetics of Its 1,3,6,8-Tetrasilylated Derivative

Citation:

Robbins SJ, Thibault ME, Masuda JD, Ward DR, Boeré RT, Dibble PW. X-ray Structures of Cyclophanes Derived from Naphtho 1,2-c:5,6-c -difuran and the Synthesis, Structure, and Reaction Kinetics of Its 1,3,6,8-Tetrasilylated Derivative. Journal of Organic Chemistry [Internet]. 2009;74:5192-5198.

Abstract:

A silylated derivative of naphtho[1,2-c:5,6-c]difuran, 1,3,6,8-tetrakis(tert-butyldimethylsilyl)naphtho[1,2-c:5,6-c]difuran, has been isolated and its X-ray crystal structure determined. Bond localization confirms the polyene character of this isobenzofuran ring system. This molecule undergoes two successive Diels-Alder reactions with second-order rate constants differing by over 2 orders of magnitude, consistent with predictions based on their structure-count ratios and with the reactivity of the novel 1,3-bis(tert-butyldimethylsilyl)isobenzofuran. Crystal structures of two cyclophanes derived from the reaction of naphtho[1,2-c:5,6-c]difuran and bis(imide) or bis(ester) dienophiles show marked differences in the conformation of the aliphatic chain found in the solid state.

Notes:

Times Cited: 1Robbins, Steven J. Thibault, Michelle E. Masuda, Jason D. Ward, David R. Boere, Rene T. Dibble, Peter W.

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