2,2'-binaphthylene phosphorochloridite (BINOL-PCI) 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)

Abstract

Primary and secondary alcohols were transformed in high yield to corresponding iodides by 4-chloro- 3,5-dioxaphosphacyclohepta [2,1-α; 3,4-α'] dinaphthalene (BINOL-PCl) at room temperature. The tertiary alcohols formed corresponding alkenes by stereo- and/or regioselective elimination reactions. (E)- 1,2-Diphenyl-1-propene and 2,3-diphenyl-1-propene were stereoselectively obtained from 1,2-diphenyl-2- propanol, as representative. No (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 α-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 α-methylene carbon chemical shift.