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Scientific article
English

Intramolecular Vinyl Radical Cyclization Reactions of Cyclohexadienes Derived from Sequential Additions to (Arene)(tricarbonyl)chromium Complexes

Published inHelvetica chimica acta, vol. 79, no. 6, p. 1533-1536
Publication date1996
Abstract

Cyclohexa-1,3-dienes 7-10 with a 1,5,6-substitution pattern were prepared in a one-pot reaction sequence by sequential addition of MeLi and propargyl bromides to the tricarbonylchromium complex 1a. These products were subjected to radical cyclization procedures. Vinyl radical generation by Bu3Sn addition to the propargyl group in 7-10 was followed by regio- and diastereoselective intramolecular ring closure. Two different 5-exo-trig cyclizations are possible via different vinyl radical intermediates and cyclization to one or the other of the termini of the cyclohexadiene moiety. Internal alkynes reacted to yield exclusively the cis-fused hexahydroindene products 12-14, whereas the terminal alkyne yielded bicyclo[3.2.1]octenes 11 as sole products.

Citation (ISO format)
BERUBEN, Dov, KUNDIG, Ernst Peter. Intramolecular Vinyl Radical Cyclization Reactions of Cyclohexadienes Derived from Sequential Additions to (Arene)(tricarbonyl)chromium Complexes. In: Helvetica chimica acta, 1996, vol. 79, n° 6, p. 1533–1536. doi: 10.1002/hlca.19960790603
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ISSN of the journal0018-019X
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