
TY  - JOUR
A1  - Moursounidis, J 
A1  - Wege, D 
T1  - A synthesis and some reactions of 7-Oxabicyclo[2.2.1]heptan-2-one
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 12
SP  - 2473
EP  - 2482
KW  - 
UR  - https://doi.org/10.1071/CH9832473 
N2  - Diels-Alder reaction between furan and &#945;-chloroacrylonitrile gives a mixture of exo-2-chloro-and endo-2-chloro-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitrile (4) and (5). Mild hydrolysis affords the corresponding &#945;-chloro acid mixture, from which the endo carboxylic acid may be removed through iodo lactone formation. Catalytic hydrogenation of (4) and (5) followed by hydrolysis, acyl azide formation, Curtius rearrangement, and hydrolysis of the resulting mixture of a-chloro isocyanates yields 7-oxabicyclo[2.2.l]heptan-2-one (1) in preparatively useful amounts. Reduction of (1) gives only endo alcohol, and Baeyer-Villiger reaction proceeds with exclusive bridgehead atom migration. Thermal decomposition of the sodium salt of the p-toluenesulfonylhydrazone of (1) affords 7-oxatricyclo[2.2.1 .02,6]heptane. 
ER  -

