55454-22-3Relevant academic research and scientific papers
PREPARATION OF ALLYL ALCOHOLS FROM MONOHALO- AND GEM-DIHALOBUTYLCYCLOPROPANES IN THE PRESENCE OF COPPER AND ITS SALTS
Korneva, O. S.,Nefedov, O. M.
, p. 2194 - 2196 (2007/10/02)
The reaction of gem-dibromo- or gem-dichlorobutylcyclopropanes with an equimolar amount of CuSO4*5H2O in a mixture of DMSO and water is accompanied by scission of the three-membered ring and formation of the corresponding 2-bromo- or 2-chloroallyl alcohols.The corresponding allyl alcohols were prepared analogously from monobromo- or monochlorocyclopropanes.
NICKEL(II)-CATALYZED ALKYLATION OF 2-METHYL-1,3-DIOXEP-4-ENE BY GRIGNARD REAGENTS: AN EFFICIENT AND SELECTIVE ROUTE TO ALLYLIC ALCOHOLS
Menicagli, Rita,Malanga, Corrado,Finato, Barbara,Lardicci, Luciano
, p. 69 - 70 (2007/10/02)
Allylic alcohols are formed, in good yields, through the regiocontrolled Cl2Nidppe-catalyzed alkylation of 2-methyl-1,3-dioxep-4-ene by Grignard reagents .Highly pure Z alcohols arise when secondary and tertiary aliphatic Grignards are used.
SYNTHESIS WITH ORGANOBORANES. I. SYNTHESIS OF ALLYLIC DIETHYLBORANES AND B-ALLYLIC BORINANES VIA METALATION OF OLEFINS. CONTRATHERMODYNAMIC ISOMERIZATION OF OLEFINS
Zaidlewicz, Marek
, p. 139 - 146 (2007/10/02)
Allylic organopotassium compounds prepared by metalation of olefins with trimethylsilylmethylpotassium reacted with chlorodiethylborane and b-chloroborinane to give allylic diethylboranes and B-allylic borinanes, respectively.Hydrolysis of these organoboranes proceeding with allylic rearrangement leads to isomerized olefins.In this way, (E,Z)-2-pentene, (Z)-2-heptene, 1-methylcyclohexene and (+)-α-pinene were cleanly transformed into 1-pentene, 1-heptene, methylenecyclohexane and (+)-β-pinene, respectively.Stereochemistry of the addition of myrtenyldiethylborane toformaldehyde and 2-cyclohexenyldiethylborane to 4-t-butylcyclohexanone is described.
(E)-1-Bromo-3,3-diethoxy-1-propene (Diethyl Acetal of 3-Bromoacrolein). A Versatile Synthon for the Synthesis of Furans, Butenolides, and (Z)-Allyl Alcohols
Meyers, A. I.,Spohn, Ronald F.
, p. 4872 - 4877 (2007/10/02)
A convenient preparation of the title compound allowed a study in which the α-lithio-α-bromovinyl acetal 2 could be evaluated as a precursor to furans, butenolides, and (Z)-allyl alcohols.Reaction of the lithio derivative with aldehydes, ketones, and alkyl halides took place in a convenient manner.The bromine was either transformed at a later stage to an alkyl group or reduced to hydrogen with tin hydrides.The carbonyl adducts of 2 could be transformed, on mild hydrolysis, to butenolides or 2,3-disubstituted furans.An interesting solvent system (1:1:1 THF-Et2O-pentane) allowed vinyl proton abstraction and halogen-metal exchange to take place in one pot.
