Scientific article

Approaches to 1H-Cyclopropa[l]phenanthrenes. Eliminations with 1a,9b-Dihydro-1H-cyclopropa[l]phenanthrene Derivatives

Published inHelvetica chimica acta, vol. 69, no. 4, p. 855-864
Publication date1986-06-18
First online date2004-10-25

Base-induced elimination of the sulfonium salt 2i in the presence of furan affords the addition products 7 and 8, derived from 1H-cyclopropa[l]phenanthrene (1) and the isomeric cyclopropene 5a(Scheme 3). Upon oxidation, the selenide 2c yields phenanthrene-9-methanol (9), presumably via1. No evidence for the intermediate 1 is obtained from sulfoxide pyrolysis with 2e, which leads to products formed by radical pathways (Scheme 5). Reductive elimination of the disulfone 3b gives half-reduction to monosulfone 2g and complete reduction to cyclopropane 2 as well as 9-methylphenanthrene (15), but no evidence for the intermediate 1.

Citation (ISO format)
MULLER, Paul, GODOY-NGUYEN THI, Huong Can, PFYFFER, Jean. Approaches to 1<i>H</i>-Cyclopropa[<i>l</i>]phenanthrenes. Eliminations with 1a,9b-Dihydro-1<i>H</i>-cyclopropa[<i>l</i>]phenanthrene Derivatives. In: Helvetica chimica acta, 1986, vol. 69, n° 4, p. 855–864. doi: 10.1002/hlca.19860690412
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Article (Published version)
ISSN of the journal0018-019X

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