102472-53-7Relevant academic research and scientific papers
Synthesis of Oxa- and Thia- analogs of Bicycloalkanes
Rao, R. R.,Sarkar, Rina,Bhattacharya, Sukla,Mukherjee, M. N.
, p. 939 - 946 (2007/10/02)
A general and convenient synthetic approach of a variety of oxa- and thia- analogs of bicycloalkanes is described.This is illustrated by the synthesis of a series of 2-oxa(IIa-d)- and 2-thia(IIa-d)- analogs of bicyclooctane(I) on one hand and 4-oxa(Va-d)- and 4-thia(VIa-d)- analogs of bicyclodecane(IV) on the other.The analogs of I and IV are obtained by cyclohydration of the diols XIX and XXI respectively usung dil.H2SO4 or DMSO.The diols in turn are prepared starting from the keto acids VII.On the otherhand, treatment of di-tosylates XX and XXII of XIX and XXI with Na2S in refluxing ethanol affords the respective 2-thia(III)- and 4-thia(VI)- analogs of I and IV systems.The formation of oxolans(II) via oxidative cyclisation of the cycloalkaneethanols(XXIII) with lead tetraacetate is also described.
