86905-84-2Relevant academic research and scientific papers
CYCLOADDITION OF DICLOROKETENE WITH FUNCTIONALIZED CYCLOALKENES. SYNTHESIS OF BICYCLOOCTANONE-3-YL DERIVATIVES AND OF 3,4-DICARBOXYMETHOXY-1-METHYLBICYCLOOCTAN-7-ONE
Rosini, Goffredo,Ballini, Roberto,Zanotti, Valerio
, p. 1085 - 1090 (2007/10/02)
Dichloroketene reacts with some cycloalkenes in wich an ester function is in homoallylic or in an even more remote position with respect to sp2 carbon atoms.In fact acetate and benzoate of 3,5,5-trimethylcyclohex-3-en-1-ol and 1,2-dicarbomethoxy-4-methyl-cyclohex-4-ene undergo 2+2 cycloaddition of dichloroketene to produce the corresponding bicyclooctanone derivatives in 60-65percent yield.In the latter case the process occurs regiospecifically to give 3,4-dicarboxymethoxy-1-methylbicyclooctan-7-one as product after dechlorination.The Hassner zinc dehalogenation method of generating dichloroketene is the best procedure.
