Tetrahedron p. 2875 - 2880 (1981)
Update date:2022-08-05
Topics:
Bertrand, G.
Manuel, G.
Mazerolles, P.
Trinquier, G.
The chemical behaviour of sila-2 butadienes, formed as transient intermediates either by thermolysis or by photolysis of various 1-vinylsilacyclobutanes, was studied with respect to hydroxylated compounds of different pKa values.Two mechanisms can explain the nature of the products obtained on the co-thermolysis of the cyclic compounds with phenol, one with 1-silacyclobut-1-ene intermediate and the other involving an allylic silicenium cation.In both hypothetical mechanisms, the 2-silabutadienes behave as a conjugated system since they lead either to <2 + 2> cycloaddition or to (1,2)- and (1,4)-electrophilic addition.This evidence for a conjugation phenomenon through a silicon atom is supported by the calculation of the delocalisation energies of butadiene and 2-silabutadiene.
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Doi:10.1021/jo00344a001
(1982)Doi:10.1002/ejoc.200400224
(2004)Doi:10.1007/BF00503536
(1981)Doi:10.1134/s1070428008020164
(2008)Doi:10.1016/S0040-4039(01)81884-0
(1981)Doi:10.1016/S0040-4020(01)91537-6
(1984)
