80252-72-8Relevant articles and documents
Nucleophile-induced ring enlargement of 1-(1-iodoalkyl)silacyclobutane and 1-(1,2-epoxyalkyl)silacyclobutane into silacyclopentane. Application to the synthesis of 1,4-diol, 4-alken-1-ol, and 1,4,5-triol
Matsumoto,Takeyama,Miura,Oshima,Utimoto
, p. 250 - 261 (2007/10/02)
Two methods for ring enlargement of silacyclobutane into silacyclopentane have been described. (1) Treatment of 1-(1-iodoalkyl)silacyclobutane with t-BuOK or AgOAc provided 2-alkyl-1-silacyclopentanes which were easily converted into 1,4-diols by oxidativ
Base-induced rearrangement of oxiranylsilacylobutane into silacyclopentane. Application to stereoselective synthesis of 4-alken-1-ol and 1,4,5-triol
Matsumoto,Takeyama,Oshima,Utimoto
, p. 4545 - 4548 (2007/10/02)
Treatment of 1-methyl-1-(cis-1,2-epoxyhexyl)-1-silacyclobutane 16a with i-PrOLi provided erythro-1-methyl-1-isopropoxy-2-(2-hydroxypentyl)-1-silacyclopentane 17a which was converted into (Z)-4-nonen-1-ol 18, (E)-4-nonen-1-ol 19, or 1,4,5-nonanetriol 20, r
LE PROBLEME DE LA CONJUGAISON A TRAVERS UN ATOME DE SILICIUM ?-LIE DANS LES SYSTEMES SILA-2 BUTADIENIQUES
Bertrand, G.,Manuel, G.,Mazerolles, P.,Trinquier, G.
, p. 2875 - 2880 (2007/10/02)
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 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.