Scientific article

exo-Stereoselectivity in Diels-Alder Addition of Halogenocyclopropenes to Butadienes and Furans

Published inHelvetica chimica acta, vol. 71, no. 3, p. 544-550
Publication date1988-05-04
First online date2004-10-25

The stereochemistry of the Diels-Alder reaction of 1,2-dichloro-3,3-difluorocyclopropene (5a) to 1,4-diphenyl-1,3-butadiene (6) and 1,3-diphenylisobenzofuran (7) was unambiguously established by X-ray structure determination. In all cases known so far, tetrahalogenocyclopropenes add exo to open-chain dienes and furans. The previously reported exo-addition product (2a) of l-bromo-2-chlorocyclopropene (5b) to 7 allows assignments of the stereochemistry of other additions of 5b to furans. exo-Addition usually predominates, but in some cases endo- adducts are also formed. This contrasts with reports in the literature that 5b adds preferentially endo to open-chain dienes.

Citation (ISO format)
MULLER, Paul et al. <i>exo</i>-Stereoselectivity in <i>Diels-Alder</i> Addition of Halogenocyclopropenes to Butadienes and Furans. In: Helvetica chimica acta, 1988, vol. 71, n° 3, p. 544–550. doi: 10.1002/hlca.19880710306
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Article (Published version)
ISSN of the journal0018-019X

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