Issue 0, 1981

Investigation of an electrocyclisation route to the 7bH-cyclopent[c,d]-indene system

Abstract

An approach to the synthesis of derivatives of 7bH-cyclopent[cd]indene ring system (1) has been explored in which two of the three rings are constructed by cyclisation reactions. The acetylenic alcohol (7) was prepared by coupling of 3-iodo-2-methylcyclopent-2-en-1-one (6) with the copper(I) salt of prop-2-ynyl alcohol tetrahydropyranyl ether. This was then converted into the Z,E-trienedione (2). On heating, this compound failed to undergo cyclisation; the only reaction observed was its isomerisation to the E,E-trienedione (10). Under forcing conditions it gave only indan -1-one.

The cis-double bond of the trienedione system was fixed by incorporating it into a bicyclo[2.2.1]heptadiene system. Two such derivatives, (14) and (15), were prepared; both underwent smooth electrocylic ring-closure on heating and the ylide (15) also cyclised further to give compound (19), which incorporates the required 7b-H cyclopent [cd]indene skeleton.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 3234-3238

Investigation of an electrocyclisation route to the 7bH-cyclopent[c,d]-indene system

R. H. Bradbury, T. L. Gilchrist and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1981, 3234 DOI: 10.1039/P19810003234

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