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2,5- And 2,6-dicyclopropylbenzoquinones from photoreaction of cyclopropylacetylene with Fe(CO)5

✍ Scribed by Rae Victor; Raphael Ben-Shoshan; Shalom Sarel

Book ID: 104238484
Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 166 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)87151-3

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✦ Synopsis

Scheme I 4 ,,R + Fe(C0)5 L 4 CRFe(CO), hu-The question whether acetylenic a-electrons might play a similar role in reactions of cyclopropylacetylene systems was the initial point of interest in the present study.

From the outset, however, it was apparent that on irradiation of cyclopropylacetylene (L)2

with Fe(C0)5 in solution (hexane or CH2C12),' only the acetylenic portion of the molecule is involved. From the reaction mixture a black organometallic material (2_) obtained directly as a precipitate (in hexane) or on evaporation of the solution (CH2C12) yielded on oxidative degradation 2,5-and 2,6-dicyclopropylbenzoquinones (3 and 3 Scheme II) in overall yield-70%.

Scheme II

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