Regioselective hydroxylations of 1,3-dienes via hydrocobaltation reactions. Facile conversion of myrcene to geraniol and to (±)-linalool
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 103-104
- https://doi.org/10.1039/c39900000103
Abstract
Regioselective (1,4-) hydrocobaltation of myrcene (1) leads to a 2 : 1 mixture of (E)- and (Z)-allylcobaloximes (2) which can be converted via the corresponding hydroxylamines (5) to geraniol (6a) and nerol (6b); by contrast, in the presence of molecular oxygen, (2) is converted into the peroxyallylcobalt complex (7), a precursor to linalool (8) and to linalool oxide (10).Keywords
This publication has 15 references indexed in Scilit:
- Cobalt-mediated reactions. A new synthetic approach to β-, γ- and δ-lactamsTetrahedron Letters, 1989
- Simonsen Lecture. Cobalt-mediated radical reactions in organic synthesisChemical Society Reviews, 1988
- Hydrocobaltation–dehydrocobaltation reactions in synthesis: a new approach to the controlled cross-coupling between sp2carbon centres leading to functionalised alkenesJournal of the Chemical Society, Chemical Communications, 1988
- Cobalt mediated radical addition–elimination carbon–carbon bond forming reactions in synthesisJournal of the Chemical Society, Chemical Communications, 1987
- Selective Hydrogenation of Conjugated Dienes Catalyzed by Thiocyanatotris(triphenylphosphine)cobalt(I)Bulletin of the Chemical Society of Japan, 1985
- Alkylation of ethyl bromomalonate by alkylcobaloximesJournal of Organometallic Chemistry, 1979
- Homolytic displacements at carbon. Part 3. Regiospecific syntheses of allyl sulphones in the reaction of allycobaloximes with organosulphonyl chloridesJournal of the Chemical Society, Perkin Transactions 1, 1979
- Homolytic displacements at carbon centres. Part 1. Reaction of allyl- and allenyl-cobaloximes with polyhalogenomethanesJournal of the Chemical Society, Perkin Transactions 2, 1979
- Allyl- and propadienyl-cobaloximes: character and reactions with tetracyanoethyleneJ. Chem. Soc., Dalton Trans., 1978
- Temperature and axial ligand dependence of the dynamic character of allylcobaloximesJournal of the American Chemical Society, 1974