
TY  - JOUR
A1  - Mander, LN 
A1  - Wilshire, C 
T1  - Studies on Intramolecular Alkylation, XI. An Adventitious Synthesis of a 1,4-Ethanopentalene Derivative from a Norbornenone-Derived Diazomethyl Ketone
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 9
SP  - 1975
EP  - 1981
KW  - 
UR  - https://doi.org/10.1071/CH9791975 
N2  - The C2-epimeric mixture of 2-chloro-7-formylbicyclo[2,2,1]hept-5-ene-2-carbonitriles (5) was homologated by simple synthetic steps to the norbornenone-derived acids (12) and (13). The diazomethyl ketone derived from (12), on treatment with BF3,Et2O in nitromethane, gave (l&#945;(,3a&#946;,4&#945;(,6a&#946;)-3,3a,4,6a-tetrahydro-1,4-ethanopentalene-2(1H),8-dione (20). Structure (20) was deduced from cleavage by sodium methoxide to a symmetrical methyl ester derived from bicyclo-[3,2,1]oct-6-en-3-one. The structure of the reported product dione (8) from the acetic acid treatment of diazoketone (7) has been revised to (21). 
ER  -

