10519-87-6Relevant articles and documents
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Kanazashi
, p. 493,494 (1953)
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NMR STUDY (1H, 13C and 29Si) OF (CH3)4-xSi(CH=CH2)x COMPOUNDS WHERE x = 0, 1, 2, 3, 4
Delmulle, L.,Kelen, G. P. van der
, p. 309 - 314 (1980)
The 1H, 13C and 29Si NMR spectra of the various methylvinylsilanes have been analysed with the aid of a special simulation program.From considerations of the chemical shifts and of the coupling constants 2,3J1H-1H, 1J13C-1H, 1J29Si-13C and 2J29Si-C-1H it is shown that a mesomeric-M effect from the vinyl group to the Me-Si group is important, in very good agreement with previously published PES results .The mesomeric interaction in this series is ascribed to a hyperconjugation in accordance with theoretical considerations .
Sila-α-galbanone and analogues: Synthesis and olfactory characterization of silicon-containing derivatives of the galbanum odorant α-galbanone
D?rrich, Steffen,Ulmer, Anna,Mahler, Christoph,Burschka, Christian,Baus, Johannes A.,Tacke, Reinhold,Chai, An,Ding, Changming,Zou, Yue,Brunner, Gerhard,Goeke, Andreas,Kraft, Philip
, p. 4394 - 4407 (2014)
Silicon compounds 1b-3b are sila-analogues of the galbanum odorants α-galbanone (1a), α-spirogalbanone (2a), and nor-α-galbanone (3a), respectively. Sila-α-galbanone (1b), sila-α-spirogalbanone (2b), and sila-nor-α-galbanone (3b) were synthesized in multistep syntheses in isomerically pure form, starting from Me2SiCl2, (CH2=CH)2SiCl2, and Me2(CH2=CH)SiCl, respectively. Hydroformylation of vinylsilanes, followed by either ring-closing aldol condensation or ring-closing alkene metathesis, were the key steps in these syntheses. The C/Si pairs 1a/1b, 2a/2b, and 3a/3b were studied for their olfactory properties. All compounds possess green-fruity galbanum-type odors with pineapple aspects and thus are olfactorily related. However, sila-analogues 1b-3b were found to be weaker than the corresponding parent carbon compounds 1a-3a. This effect is most pronounced for the C/Si pair 2a/2b as indicated by the odor thresholds of 0.023 ng L-1 air (2a) and 3.8 ng L-1 air (2b). However, due to their higher molecular mass, the silicon compounds are less volatile and thus more substantive in functional applications. In contrast to the stable 5-silacyclohex-1-enes 1b and 2b, the 4-silacyclopent-1-ene 3b shows a limited chemical stability. For compound 3a an extremely low odor threshold of 0.0087 ng L-1 air was measured, and the silicon analogue 3b with an odor threshold of 0.085 ng L-1 air is the sila-odorant with the lowest odor threshold measured so far. Sila-α-galbanone, sila-α-spirogalbanone, and sila-nor-α-galbanone (sila-analogues of α-galbanone, α-spirogalbanone, and nor-α-galbanone) were synthesized starting from Me2SiCl2, (CH2=CH)2SiCl2, and Me2(CH2=CH)SiCl, respectively. These sila-analogues proved to be less volatile and thus more tenacious than the parent carbon compounds while also providing insight into structure-odor correlations.
FRAGRANCE
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Page/Page column 6, (2015/07/07)
A chemical compound of the formula (I) in which R1 and R2 are independently selected from C1±C3 alkyl, or R1 and R2 together with the silicon atom to which they are joined form a 5 to 6 membered ring, the ring, apart from the silicon atom, consisting completely of hydrocarbon atoms, and their preparation via hydroformylation of divinylsilanes such as dialkyldivinylsilane, dichlorodivinylsilane, or 1,1-divinylsilolane with subsequent aldol condensation and Grignard reaction. The compounds of formula I are useful in fragrance applications for incorporation into fine and functional fragrances.
REACTIVITY OF Si-H BONDS IN ORGANOSILANES
Zhun', V. I.,Zhun', A. B.,Vlasenko, S. D.,Belorusskaya, L. A.,Chernyshev, E. A.,Sheludyakov, V. D.
, p. 2266 - 2270 (2007/10/02)
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