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

doi:https://doi.org/10.3906/sag-1206-65

Makale detayları

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)

Yazarlar:

Nader Noroozi PESYAN | Jabbar Khalafy And Hossein KHANI-MEINAGH

Yayıncı:

TUBITAK

Ana Başlıklar:

Kimya ve ilgili bilimler

Dergi:

Turkish Journal of Chemistry 2009 Vol.33 Issue 4, pp.527-543

Belge Tipi:

Makale

Yayın Tarihi:

3/2009

Belge Dili:

İngilizce

Document ID (Org No.):

2000728265

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/sag-1206-65

Özet:

 

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.

 

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.

Makale detayları

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)

Yazarlar: Nader Noroozi PESYAN | Jabbar Khalafy And Hossein KHANI-MEINAGH

Yayıncı: TUBITAK

Ana Başlıklar: Kimya ve ilgili bilimler

Dergi: Turkish Journal of Chemistry 2009 Vol.33 Issue 4, pp.527-543

Belge Tipi: Makale

Yayın Tarihi: 3/2009

Belge Dili: İngilizce

Document ID (Org No.): 2000728265

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/sag-1206-65

Sayı

Yazarlar:

Nader Noroozi PESYAN | Jabbar Khalafy And Hossein KHANI-MEINAGH

Yayıncı:

TUBITAK

Ana Başlıklar:

Kimya ve ilgili bilimler

Dergi:

Turkish Journal of Chemistry 2009 Vol.33 Issue 4, pp.527-543

Belge Tipi:

Makale

Yayın Tarihi:

3/2009

Belge Dili:

İngilizce

Document ID (Org No.):

2000728265

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/sag-1206-65