A facile synthesis of bicyclo [mn 1] alkan-1-ols. Evidence for organosamarium intermediates in the samarium (II) iodide promoted intramolecular Barbier-type reaction
GA Molander, JA McKie
Index: Molander, Gary A.; McKie, Jeffrey A. Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4112 - 4120
Full Text: HTML
Citation Number: 149
Abstract
Samarium (II) iodide (SmI. j has been succB88fuuy employed as a reductive coupling agent for the intramolecular Barbier-type syntheah of bicyclo [mnl] alkan-l-ola Thus, a variety of%(eiodoeJkyl) cycloakanonea, upon treatment with SmIz and a catalytic quantity of iron complex in tetrahydrofuran (THF), provide the title compounds in excellent yields. The reaction is quite general for the construction of diverse bicyclic ring systems, including the ...
Related Articles:
Solvolysis of bicyclo [4.2. 0] octane-1-methyl p-toluenesulfonate
[Dauben,W.G.; Chitwood,J.L. Journal of the American Chemical Society, 1970 , vol. 92, # 6 p. 1624 - 1629]