Controlling factors determining the selective HSCN addition to double bonds and their application to the synthesis of 7-isothiocyano-7,8-alpha-dihydro-bisabolene.

dc.creatorde Oliveira, CM
dc.creatorda Silva, CC
dc.creatorCollins, CH
dc.creatorMarsaioli, AJ
dc.date2001
dc.dateJUL-AUG
dc.date2014-11-17T00:58:46Z
dc.date2015-11-26T17:52:14Z
dc.date2014-11-17T00:58:46Z
dc.date2015-11-26T17:52:14Z
dc.date.accessioned2018-03-29T00:35:40Z
dc.date.available2018-03-29T00:35:40Z
dc.identifierJournal Of The Brazilian Chemical Society. Soc Brasileira Quimica, v. 12, n. 5, n. 661, n. 666, 2001.
dc.identifier0103-5053
dc.identifierWOS:000170611400008
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/57092
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/57092
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/57092
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1290186
dc.descriptionThe 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-alpha -bisabolene using bisabolol as starting material, was planned and successfully accomplished.
dc.description12
dc.description5
dc.description661
dc.description666
dc.languageen
dc.publisherSoc Brasileira Quimica
dc.publisherSao Paulo
dc.publisherBrasil
dc.relationJournal Of The Brazilian Chemical Society
dc.relationJ. Braz. Chem. Soc.
dc.rightsaberto
dc.sourceWeb of Science
dc.subjectterpenes
dc.subjectHSCN
dc.subjectdouble bonds
dc.subjectchemoselectivity
dc.subjectCorresponding C-10 Epimers
dc.subject(+/-)-axisonitrile-1
dc.subjectSesquiterpenoids
dc.subject(+/-)-axamide-1
dc.subjectRoute
dc.titleControlling factors determining the selective HSCN addition to double bonds and their application to the synthesis of 7-isothiocyano-7,8-alpha-dihydro-bisabolene.
dc.typeArtículos de revistas


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