Convergent Synthesis and Characterization of Organotin Dendrimers Sn{(CH2)nSn[(CH2)4SnPh3]3}4 (n = 3, 4)
摘要:
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.
Convergent Synthesis and Characterization of Organotin Dendrimers Sn{(CH2)nSn[(CH2)4SnPh3]3}4 (n = 3, 4)
摘要:
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.
Convergent Synthesis and Characterization of Organotin Dendrimers Sn{(CH<sub>2</sub>)<i><sub>n</sub></i>Sn[(CH<sub>2</sub>)<sub>4</sub>SnPh<sub>3</sub>]<sub>3</sub>}<sub>4</sub> (<i>n</i> = 3, 4)
作者:Herbert Schumann、Yilmaz Aksu、Birgit C. Wassermann
DOI:10.1021/om0602005
日期:2006.7.1
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.