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 KALAPHY
HOSSEIN KHANI-MEINAGH

DOI

10.3906/kim-0804-19

Abstract

Primary and secondary alcohols were transformed in high yield to corresponding iodides by 4-chloro-3,5-dioxaphosphacyclohepta [2,1-\alpha; 3,4-\alpha'] 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. ^{13}C chemical shifts for the \alpha-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 \alpha-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.

First Page

527

Last Page

543

Recommended Citation

NOROOZI-PESYAN, NADER; KALAPHY, JABBAR; and KHANI-MEINAGH, HOSSEIN (2009) "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)," Turkish Journal of Chemistry: Vol. 33: No. 4, Article 10. https://doi.org/10.3906/kim-0804-19
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss4/10