Synthesis and characterization of alpha,omega-bis[tri-(w-triphenylstannyl)butylstannyl]alkanes as starting materials for organotin dendrimers

Aksu Y., Aksu S., Schumann H.

APPLIED ORGANOMETALLIC CHEMISTRY, cilt.21, sa.7, ss.521-530, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 21 Sayı: 7
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1002/aoc.1251
  • Dergi Adı: APPLIED ORGANOMETALLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.521-530
  • Anahtar Kelimeler: dendrimers, organotin compounds, NMR, MS, TIN-DENDRIMERS, CHEMISTRY, MACROCYCLES, RECOGNITION, DERIVATIVES, COMPLEXES
  • Akdeniz Üniversitesi Adresli: Evet

Özet

Ph3Sn(CH2)(m)CH=CH2 [m = 2 (1a), 3 (1b)] reacts with Ph3SnH, yielding Ph3Sn(CH2)(n)SnPh3 [n = 4 (2a), 5(2b)],which in turn reacts with CH3COOH or HCl, producing (CH3CO2)(3)Sn(CH2)(n)Sn(O2CCH3)(3) (3a, b) and Cl3Sn(CH2)(n)SnCl3 (4a, b), respectively. Alkylation of compounds 4 with BrMg(CH2)(2) CH=CH2 affords (CH2=CHCH2CH2)(3)Sn(CH2)(n)Sn(CH2CH2CH=CH2)(3) (5a,b). Hydrostannylation of 5a, b with Ph3SnH results in the formation of [Ph3Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4) SnPh3](3) (6a, b) which on agitation with HCl gives [ClPh2Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4)SnPh2Cl](3) (7a, b). Hydrogenation of 7a and 7b with LiAlH4 leads to [HPh2Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4)SnPh2H](3) (8a, b), which on further reaction with CH2=CHCH2OH yields [HO(CH2)(3)Ph2Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4)SnPh2(CH2)(3)OH](3) (9a, b). All compounds were characterized by multinuclear NMR studies (H-1, C-13, Sn-119), mass spectrometry (MALDI-TOF, EI) and elemental analyses. Copyright (c) 2007 John Wiley & Sons, Ltd.

Ph3Sn(CH2)(m)CH=CH2 [m = 2 (1a), 3 (1b)] reacts with Ph3SnH, yielding Ph3Sn(CH2)(n)SnPh3 [n = 4 (2a), 5(2b)],which in turn reacts with CH3COOH or HCl, producing (CH3CO2)(3)Sn(CH2)(n)Sn(O2CCH3)(3) (3a, b) and Cl3Sn(CH2)(n)SnCl3 (4a, b), respectively. Alkylation of compounds 4 with BrMg(CH2)(2) CH=CH2 affords (CH2=CHCH2CH2)(3)Sn(CH2)(n)Sn(CH2CH2CH=CH2)(3) (5a,b). Hydrostannylation of 5a, b with Ph3SnH results in the formation of [Ph3Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4) SnPh3](3) (6a, b) which on agitation with HCl gives [ClPh2Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4)SnPh2Cl](3) (7a, b). Hydrogenation of 7a and 7b with LiAlH4 leads to [HPh2Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4)SnPh2H](3) (8a, b), which on further reaction with CH2=CHCH2OH yields [HO(CH2)(3)Ph2Sn(CH2)(4)](3)Sn(CH2)(n)Sn[(CH2)(4)SnPh2(CH2)(3)OH](3) (9a, b). All compounds were characterized by multinuclear NMR studies (H-1, C-13, Sn-119), mass spectrometry (MALDI-TOF, EI) and elemental analyses. Copyright (c) 2007 John Wiley & Sons, Ltd