Investigation of an Electrocyclisation Route to the 7bH-Cyclopentindene System

DOI: 10.1039/P19810003234

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 3234 - 3238 (1981)

Update date:2022-08-04

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Authors:

Bradbury, Robert H.

Gilchrist, Thomas L.

Rees, Charles W.

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Article abstract of DOI:10.1039/P19810003234

An approach to the synthesis of derivatives of 7bH-cyclopentindene 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 electrocyclic ring-closure on heating and the ylide (15) also cyclised further to give compound (19), which incorporates the required 7bH-cyclopentindene skeleton.

Full text of DOI:10.1039/P19810003234

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