2,2 -Binaphthylene phosphorochloridite (BINOL-PCl) as a bulky and efficient reagent for the conversion of primary and secondary alcohols into iodides, and tertiary alcohols stereo- and/or regioselectively into olefin(s)

Authors : Nader Noroozi PESYAN, Jabbar Khalafy And Hossein KHANIMEINAGH

Pages : 527-543

Doi:10.3906/sag-1206-65

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Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Primary and secondary alcohols were transformed in high yield to corresponding iodides by 4-chloro-3,5-dioxaphosphacyclohepta [2,1-a; 3,4-a`] dinaphthalene insert ignore into journalissuearticles values(BINOL-PCl); at room temperature. The tertiary alcohols formed corresponding alkenes by stereo- and/or regioselective elimination reactions. insert ignore into journalissuearticles values(E);-1,2-Diphenyl-1-propene and 2,3-diphenyl-1-propene were stereoselectively obtained from 1,2-diphenyl-2-propanol, as representative. No insert ignore into journalissuearticles values(Z);-1,2-diphenyl-1-propene was observed. 2-Methyl-1-phenylcyclopentene and 3-methyl-2-phenylcyclopentene were regioselectively obtained from 2-methyl-1-phenylcyclopentanol. 13C chemical shifts for the a-methylene carbon of some alkyl iodides empirically calculated through a very simple additive relationship lead to similar or even better values than the reported values. All primary alkyl iodides showed the iodine heavy atom effect on the a-methylene carbon chemical shift.
Keywords : Alkyl iodide, 2, 2` dihydroxy 1, 1` dinaphthalene BINOL, 2, 2` binaphthylene phosphorochloridite BINOL PCl, stereoselective, anti E2 elimination reaction, heavy