Naphtho [1, 8] bicyclo [3.2. 0] hepta-2, 6-diene. Synthesis and rearrangement to pleiadiene

J Meinwald, GE Samuelson…

Index: Meinwald,J. et al. Journal of the American Chemical Society, 1970 , vol. 92, # 26 p. 7604 - 7606

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Citation Number: 35

Abstract

The intriguing chemical possibilities for 1 led us to seek a more convenient synthesis. The method of choice was suggested by a recent report concerning heavy-atom solvent effects on the photochemical cycloaddition of acenaphthylene to acrylonitrile. 6 Thus, we were able to obtain adduct 6 from acenaphthylene and maleic anhydride using n-propyl bromide as a solvent, and to synthesize 1 by the route shown in Chart 11. chart I1