Effect of various substituents on intramolecular 1,1-vinylboration, synthesis of 1-silacyclobutene derivatives

Ezzat KHAN; Bernd WRACKMEYER

Makale detayları

Effect of various substituents on intramolecular 1,1-vinylboration, synthesis of 1-silacyclobutene derivatives

Yazarlar:

Ezzat KHAN | Bernd WRACKMEYER

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2010 Vol.34 Issue 5, pp.793-803

Belge Tipi:

Makale

Yayın Tarihi:

4/2010

Belge Dili:

İngilizce

Document ID (Org No.):

2000727992

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

The reaction of 1-boryl-1-alkenyl chlorosilane derivatives  with alkynyllithium reagents [Li-C\equiv C-R3 (R3~=~Ph, SiMe3)] at  low temperature (--78 °C) affords alkenyl(alkyn-1-yl)silanes.  These  compounds are precursors of 1-silacyclobutene derivatives, which are  formed via intramolecular 1,1-vinylboration.  This reaction works for  various groups at silicon (R1/R2: R1 = H, Me, Ph; R2 = Me, Ph) and  at the C=C and C\equiv C units (R/R3: R = nBu, Ph; R3 = nBu, Ph,  SiMe3).  The conversion into 1-silacyclobutene derivatives is  incomplete only in the case of R3 = SiMe3.  The reactions were  monitored by NMR spectroscopy in order to elucidate the reaction  mechanism, and the proposed structures of all new compounds follow  from consistent sets of NMR parameters (1H-, 13C-, 11B-,  29Si-NMR).

 

The reaction of 1-boryl-1-alkenyl chlorosilane derivatives  with alkynyllithium reagents [Li-C\equiv C-R3 (R3~=~Ph, SiMe3)] at  low temperature (--78 °C) affords alkenyl(alkyn-1-yl)silanes.  These  compounds are precursors of 1-silacyclobutene derivatives, which are  formed via intramolecular 1,1-vinylboration.  This reaction works for  various groups at silicon (R1/R2: R1 = H, Me, Ph; R2 = Me, Ph) and  at the C=C and C\equiv C units (R/R3: R = nBu, Ph; R3 = nBu, Ph,  SiMe3).  The conversion into 1-silacyclobutene derivatives is  incomplete only in the case of R3 = SiMe3.  The reactions were  monitored by NMR spectroscopy in order to elucidate the reaction  mechanism, and the proposed structures of all new compounds follow  from consistent sets of NMR parameters (1H-, 13C-, 11B-,  29Si-NMR).

Makale detayları

Effect of various substituents on intramolecular 1,1-vinylboration, synthesis of 1-silacyclobutene derivatives

Yazarlar: Ezzat KHAN | Bernd WRACKMEYER

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2010 Vol.34 Issue 5, pp.793-803

Belge Tipi: Makale

Yayın Tarihi: 4/2010

Belge Dili: İngilizce

Document ID (Org No.): 2000727992

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Ezzat KHAN | Bernd WRACKMEYER

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2010 Vol.34 Issue 5, pp.793-803

Belge Tipi:

Makale

Yayın Tarihi:

4/2010

Belge Dili:

İngilizce

Document ID (Org No.):

2000727992

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527