TY - JOUR
T1 - The chemistry of terpenes. Part 25. A synthesis of car-2-, car-3-, and car-3(10)-ene (β-carene)
AU - Cocker, Wesley
AU - Geraghty, Niall W.A.
AU - Grayson, David H.
PY - 1978
Y1 - 1978
N2 - Reaction of dibromocarbene with 4,4-dimethoxycyclohexene (7) affords 3,3-dimethoxy-7,7-dibromobicyclo-[4.1.0]heptane (8), which with lithium dimethylcuprate(II) and methyl iodide, and treatment of the product with acid, yields 7,7-dimethylbicyclo[4.1.0]heptan-3-one, ±(2). In the absence of methyl iodide, 7-exo-methylbicyclo[4.1.0]heptan-3-one, ±(12), is the major product. Treatment of the ketone (2) with methylenetriphenylphosphorane gives car-3(10)-ene (β-carene) (11) and reaction of the ketone ±(2) with methylmagnesium iodide affords the epimeric caran-3-ols (13) and (14). On dehydration these yield a mixture of carenes.
AB - Reaction of dibromocarbene with 4,4-dimethoxycyclohexene (7) affords 3,3-dimethoxy-7,7-dibromobicyclo-[4.1.0]heptane (8), which with lithium dimethylcuprate(II) and methyl iodide, and treatment of the product with acid, yields 7,7-dimethylbicyclo[4.1.0]heptan-3-one, ±(2). In the absence of methyl iodide, 7-exo-methylbicyclo[4.1.0]heptan-3-one, ±(12), is the major product. Treatment of the ketone (2) with methylenetriphenylphosphorane gives car-3(10)-ene (β-carene) (11) and reaction of the ketone ±(2) with methylmagnesium iodide affords the epimeric caran-3-ols (13) and (14). On dehydration these yield a mixture of carenes.
UR - https://www.scopus.com/pages/publications/0345610054
U2 - 10.1039/p19780001370
DO - 10.1039/p19780001370
M3 - Article
AN - SCOPUS:0345610054
SN - 1472-7781
SP - 1370
EP - 1372
JO - Journal of the Chemical Society - Perkin Transactions 1
JF - Journal of the Chemical Society - Perkin Transactions 1
IS - 11
ER -