61341-83-1Relevant academic research and scientific papers
Oxygen Participation Induced by Increased Electron Demand
Lambert, Joseph B.,Larson, Eric G.
, p. 7546 - 7550 (2007/10/02)
cis,endo-7-Oxabicyclohepta-2,3-diyl dibrosylate (6) acetolyzes faster than its diexo isomer (exo/endo ratio of 0.68 at 25 deg C).In the corresponding monobrosylate series, the exo isomer acetolyzes more rapidly than the endo isomer (exo/endo ratio
A Synthesis and Some Reactions of 7-Oxabicycloheptan-2-one
Moursounidis, John,Wege, Dieter
, p. 2473 - 2482 (2007/10/02)
Diels-Alder reaction between furan and α-chloroacrylonitrile gives a mixture of exo-2-chloro- and endo-2-chloro-7-oxabicyclohept-5-ene-2-carbonitrile (4) and (5).Mild hydrolysis affords the corresponding α-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 α-chloro isocyanates yields 7-oxabicycloheptan-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-oxatricyclo2,6>heptane.
