dc.contributor.author | Morrill, Terence | en_US |
dc.contributor.author | D'Souza, Christopher | en_US |
dc.contributor.author | Yang, Lu | en_US |
dc.contributor.author | Sampognaro, Anthony | en_US |
dc.date.accessioned | 2006-07-19T18:39:26Z | en_US |
dc.date.available | 2006-07-19T18:39:26Z | en_US |
dc.date.issued | 2002-04-19 | en_US |
dc.identifier.citation | The Journal of Organic Chemistry 67N8 (2002) 2481-2484 | en_US |
dc.identifier.issn | 1520-6904 | en_US |
dc.identifier.uri | http://hdl.handle.net/1850/2140 | en_US |
dc.description.abstract | When hydroboration of 1-octene is carried out in the presence of catalytic amounts of rhodium trichloride followed by the usual oxidation (hydrogen peroxide in aqueous alkali), only minor proportions of 1-octanol (2.4%) are formed accompanied by very significant amounts of 2- (17.4%), 3- (36.9%), and 4-octanol (43.3%). These product compositions are obtained in good overall yield when the borane-THF complex is slowly added to a stirred solution of 1-octene in THF solvent containing the rhodium trichloride. Isomerization of 1-octene to 2-, 3-, and 4-octene in the presence of rhodium trichloride alone is far too slow to account for the foregoing results. The mechanism likely involves multiple and reversible addition/elimination of a Rh-activated B-H species across the double bonds. | en_US |
dc.format.extent | 31371 bytes | en_US |
dc.format.mimetype | application/pdf | en_US |
dc.language.iso | en_US | en_US |
dc.publisher | The American Chemical Society: The Journal of Organic Chemistry | en_US |
dc.subject | Regioselectivity | en_US |
dc.subject | Rh-activated B-H species | en_US |
dc.title | Transition-metal-promoted hydroboration of alkenes: a unique reversal of regioselectivity | en_US |
dc.type | Abstract | en_US |
dc.identifier.url | http://dx.doi.org/10.1021/jo0109321 | |