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Site‐Selective Hydrosilylation of Botryococcene ‐ The Algal Biomass Hydrocarbon Oil
Author(s) -
Kawashima Hidehisa,
Umezawa Mami,
Kijima Masashi
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702686
Subject(s) - hydrosilylation , olefin fiber , moiety , chemistry , carbon skeleton , double bond , triterpene , carbon fibers , hydrocarbon , biomass (ecology) , organic chemistry , catalysis , molecule , materials science , geology , medicine , alternative medicine , oceanography , pathology , composite number , composite material
An algal acyclic triterpene botryococcene (( E )‐2,3,7,10,13,16,20,21‐octamethyl‐6,17‐dimethylene‐10‐vinyldocosa‐1,11,21‐triene), new biomass for material sources, which has three‐types of six carbon‐carbon double bonds, i. e., four vinylidenes at C2,6,17,21‐positions, one C10‐vinyl, and one C11‐12 internal olefin, in the molecule underwent hydrosilylation of various organosilanes in the presence of Pt(0) 1,3‐divinyl‐1,1,3,3‐tetramethyldisiloxane complex (Karstedt's catalyst). Various hydrosilylated botryococcene derivatives were site‐ and regioselectively obtained in high yields by an anti ‐Markovnikov type addition at the C10‐vinyl moiety without any isomerizations of the unsaturated triterpenoid skeleton.