- Turkish Journal of Chemistry
- Vol: 33 Issue: 4
- 2,2 -Binaphthylene phosphorochloridite (BINOL-PCl) as a bulky and efficient reagent for the conversi...
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 Khani-meinagh
Pages : 527-543
Doi:10.3906/sag-1206-65
View : 11 | Download : 6
Publication Date : 9999-12-31
Article Type : Makaleler
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 (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 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 atom effect.