Controlling factors determining the selective HSCN addition to double bonds and their application to the Synthesis of 7-Isothiocyano-7,8-α-Dihydro-Bisabolene
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Data
2001-08
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Resumo
The reactivity of terminal and trisubstituted double bonds of monoterpenes with HSCN has
been examined by GC giving evidence that kinetics is responsible for the chemoselective addition
to terminal double bonds in terpenes. The results show that the addition to the terminal double
bond is about 17 times faster than for trisubstituted double bonds and that the presence of the first
SCN group in the molecule prevents a second addition. The presence of a hydroxyl or methoxy
group in the molecule, decreases the reaction kinetics. Based on these kinetic experiments a two
steps synthesis of the natural product 7-isothiocyano-7,8-dihydro- -bisabolene using bisabolol
as starting material, was planned and successfully accomplished.
Descrição
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Terpenes, HSCN, Double bonds, Chemoselectivity
Citação
OLIVEIRA, Cecília M. de et al. Controlling factors determining the selective HSCN addition to double bonds and their application to the Synthesis of 7-Isothiocyano-7,8-α -Dihydro-Bisabolene. Journal of the Brazilian Chemical Society, Campinas, v. 12, n. 5, p. 661-666, Aug. 2001.