Convergent synthesis and characterization of organotin dendrimers Sn{(CH2)(n)Sn[(CH2)(4)SnPh3](3)}(4) (n=3, 4)

Schumann H., AKSU Y., Wassermann B. C.

ORGANOMETALLICS, cilt.25, sa.14, ss.3428-3434, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 25 Sayı: 14
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1021/om0602005
  • Dergi Adı: ORGANOMETALLICS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3428-3434
  • Akdeniz Üniversitesi Adresli: Hayır

Özet

The reaction of the omega-haloalkyltin trihalides Br(CH2)(3)SnBr3 and Br(CH2)(4)SnBr3 with 3 equiv of but-3-enylmagnesium bromide yielded Br(CH2)(3)Sn(CH2CH2CH=CH2)(3) ( 3) and Br(CH2)(4)Sn(CH2CH2CH=CH2) (3) (4). Both dendritic branches can be converted into their corresponding Grignard reagents, whose consequent treatment with 0.25 M amounts of SnCl4 resulted in the formation of the dendrimers Sn[(CH2)(3)Sn(CH2CH2CH=CH2)(3)](4) (5) and Sn[(CH2)(4)Sn(CH2CH2CH=CH2)(3)](4) ( 6), respectively. The subsequent hydrostannation of 5 and 6 delivered Sn {(CH2)(3)Sn[(CH2)(4)SnPh3](3)}(4) ( 7) and Sn {(CH2)(4)Sn[(CH2)(4)SnPh3](3)}(4) ( 8) as dendrimers of the second generation. All compounds were characterized by elemental analysis, H-1, C-13, and Sn-119 NMR spectroscopy, and MALDI-TOF mass spectrometry.

The reaction of the omega-haloalkyltin trihalides Br(CH2)(3)SnBr3 and Br(CH2)(4)SnBr3 with 3 equiv of but-3-enylmagnesium bromide yielded Br(CH2)(3)Sn(CH2CH2CH=CH2)(3) ( 3) and Br(CH2)(4)Sn(CH2CH2CH=CH2) (3) (4). Both dendritic branches can be converted into their corresponding Grignard reagents, whose consequent treatment with 0.25 M amounts of SnCl4 resulted in the formation of the dendrimers Sn[(CH2)(3)Sn(CH2CH2CH=CH2)(3)](4) (5) and Sn[(CH2)(4)Sn(CH2CH2CH=CH2)(3)](4) ( 6), respectively. The subsequent hydrostannation of 5 and 6 delivered Sn {(CH2)(3)Sn[(CH2)(4)SnPh3](3)}(4) ( 7) and Sn {(CH2)(4)Sn[(CH2)(4)SnPh3](3)}(4) ( 8) as dendrimers of the second generation. All compounds were characterized by elemental analysis, H-1, C-13, and Sn-119 NMR spectroscopy, and MALDI-TOF mass spectrometry.