TY - JOUR
T1 - Cyclisation of 5-Bromomethyl-Cycloheptene and -Cyclo-Octene
T2 - A New Route to Bicyclo[3.2.1]Octanes and Bicyclo[4.2.1]Nonanes
AU - MacCorquodale, Finlay
AU - Walton, John C.
PY - 1989/1/1
Y1 - 1989/1/1
N2 - Reduction of 5-(bromomethyl)cycloheptene with tributyltin hydride gave bicyclo[3.2.1 ] octane; similar reduction of 5-(bromomethyl)cyclo-octene gave bicyclo[4.2.1 ]nonane together with some bicyclo[3.3.1 Jnonane. The cyclohept-4-enylmethyl radical intermediate exists as a rapidly equilibrating mixture of conformers, including the axial boat form from which cyclisation occurs. The rates of the two main cyclisation reactions are ca. 105 s_1 at 25 °C. Condensation of the dimethylamine enamine of 4-methylcyclohexanone with acrylaldehyde and subsequent treatment with methyl iodide and base gave 6-methyloctahydro-1 -benzopyran-2-one.
AB - Reduction of 5-(bromomethyl)cycloheptene with tributyltin hydride gave bicyclo[3.2.1 ] octane; similar reduction of 5-(bromomethyl)cyclo-octene gave bicyclo[4.2.1 ]nonane together with some bicyclo[3.3.1 Jnonane. The cyclohept-4-enylmethyl radical intermediate exists as a rapidly equilibrating mixture of conformers, including the axial boat form from which cyclisation occurs. The rates of the two main cyclisation reactions are ca. 105 s_1 at 25 °C. Condensation of the dimethylamine enamine of 4-methylcyclohexanone with acrylaldehyde and subsequent treatment with methyl iodide and base gave 6-methyloctahydro-1 -benzopyran-2-one.
UR - http://www.scopus.com/inward/record.url?scp=37049067506&partnerID=8YFLogxK
U2 - 10.1039/P19890000347
DO - 10.1039/P19890000347
M3 - Article
AN - SCOPUS:37049067506
SN - 1470-4358
SP - 347
EP - 352
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 2
ER -