130460-83-2Relevant academic research and scientific papers
Silaheterocycles VII; Reactions of Dichloroneopentylsilene with Aldehydes
Auner, Norbert,Seidenschwarz, Claudia
, p. 909 - 920 (2007/10/02)
Dichloroneopentylsilene, Cl2Si=CHCH2But (1), is produced from vinyltrichlorsilane (2) and LiBut in n-pentane at -78 deg C.The reactions of 1 with aromatic aldehydes like benzaldehyde and the 4-methoxy- or 4-fluoro-substituted derivatives, naphthalene-1 and -2- and 9-anthracenecarbaldehyde, furfurale and its S-analogous thiophene carbaldehyde yield 1,2-silaoxetanes by cycloaddition with the carbonyl group.The same is true for the reactions of 1 with pivaline-, butyr- and acetaldehyde.The silaoxetanes cannot be isolated; the formation of dichlorovinylsiloxanes and the olefinic compounds R-CH=CH-CH2But suggests that the cycloreversion of the Si-O four-membered ring competes with an intramolecular isomerization, evidently via formation of a zwitterionic intermediate R-C+HOSiCl2C-HCH2But.The product formation by coupling reactions of lithiated aldehydes and 2 is excluded by performing analogous reactions with the chlorosilanes Me2SiCl(R) (R=Cl, Me, Vi).
