Nader Noroozi PESYAN, Jabbar Khalafy And Hossein KHANI-MEINAGH

133129

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)

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.

Anahtar Kelimeler:

Alkyl iodide, 2, 2'-dihydroxy-1, 1'-dinaphthalene (BINOL), 2, 2'-binaphthylene phosphorochloridite (BINOL-PCl), stereoselective, anti-E2 elimination reaction, heavy atom effect.

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)

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.,

Turkish Journal of Chemistry-Cover

ISSN: 1300-0527
Yayın Aralığı: 6
Yayıncı: TÜBİTAK

Arşiv

Sayıdaki Diğer Makaleler

Photochemical bromination of substituted indan-1-one derivatives: synthesis of new polybromoindan-1-one derivatives

Nermin Şimşek KUŞ

Synthesis and in vitro anti-Helicobacter pylori activity of 2-(substituted benzylthio)-5-(5-nitro-2- furyl)-1, 3, 4-thiadiazole derivatives

Negar MOHAMMADHOSSEINI, Ali ASADIPOUR, Bahram LETAFAT

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)

Nader Noroozi PESYAN, Jabbar Khalafy And Hossein KHANI-MEINAGH

One-pot synthesis of amidoalkyl naphthols using NaHSO4.SiO2 as an efficient and recyclable heterogeneous catalyst

Hamid Reza SHATERIAN, Hossein Yarahmadi And Majid GHASHANG

Synthesis and characterization of new optically active and heat resistant poly (amide-imide)s derived from N,N'-bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic)-bis-L-leucine and aromatic diamines

Hossein Nasr ISFAHANI, Atena IZADKHAH, Khalil FAGHIHI, Meisam SHABANIAN

Application of FAM ligands in the metal-promoted catalytic enantioselective synthesis of organic compounds

Özdemir DOĞAN, Philip P. GARNER, Adnan BULUT

Zeolite catalyzed efficient synthesis of perimidines at room temperature

Akbar MOBINIKHALEDI, Naser FOROUGHIFAR, Nemat BASAKI

Performance analysis for direct 2-propanol fuel-cell based on Pt containing anode electrocatalysts

Niyazi Alper TAPAN, Ezgi ÖZTÜRK

Comparative study of selective CO oxidation over Pt-Co-M/ $Al_2O_3$ catalysts (M=Ce, Mg, Mn, Zr, Fe) in hydrogen-rich streams: effects of a second promoter

Ramazan YILDIRIM, K. Erdem UĞUZ

Study of binary complexes of nickel(II), copper(II), and vanadium(V) with acetazolamide in aqueous medium by voltammetry