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| - Synthesis of a C44H26 Hydrocarbon Having a Carbon FrameworkRepresented on the Surface of C60 via Benzoenyne-Allenes
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| - The C44H26 hydrocarbon 20 was synthesized in 13% overall yield in eight steps from acenaphthenequinone (6) and 2 equiv of 1-(2-ethynylphenyl)-2-phenylethyne. Condensation of the monoketal7 with the lithium acetylide 8 afforded the benzoenediynyl propargylic alcohol 9. On exposure tothionyl chloride, 9 underwent a cascade of reactions with the formation of the chloro-substitutedbenzoenyne-allene 11 in situ followed by a C2−C6 cyclization to produce the biradical 12, leadingto the formal Diels−Alder adduct 13 and subsequently, after tautomerization, the chloride 14.Reduction with sodium borohydride then gave 15. Deprotection of the ketal group produced 16 toallow a repeat of condensation with the acetylide 17 followed by the cascade transformation toafford the chloride 19. Subsequent reduction then furnished the C44H26 hydrocarbon 20 having acarbon framework represented on the surface of C60.
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