76001-74-6Relevant articles and documents
REACTIVITY OF ORGANOTIN COMPOUNDS. XX. ACYLDEMETALLATION OF RSnMe3 compounds
Kashin, A. N.,Bumagin, N. A.,Kalinovskii, I. O.,Beletskaya, I. P.,Reutov, O. A.
, p. 1329 - 1334 (2007/10/02)
The reactions of RSnMe3 with R=CH3 (I), C4H9 (II), C6H5 (III), 9-fluorenyl (IV), 9-methyl-9-fluorenyl (V), indenyl (VI), and C6H5CC (VII) with acetyl chloride (VIII), benzoyl chloride (IX), and trifluoroacetic anhydride (X) in methylene chloride at room temperature, leading to the formation of unsymmetrical ketones, were investigated.It was shown that the reactions of (I-III) with (VIII-X) and also of (VII) with (VIII) and (IX) only occur in the presence of aluminium chloride, whereas a catalyst is not required for the reactions of (VI) and (VII) with (X).Compounds(IV-VI) react with (VIII) and (IX) only in presence of Et4NCl or Bu4NBr, and this is explained by the participation of ion pairs R-+Sn(CH3)3, formed by coordination of the halide ion at the tin atom and possessing higher nucleophilicity than the covalent form RSn(CH3)3.The formation of 8-methyl-8-acetoxybenzofulvene in the reaction of (VI) with (VIII) shows that metallation of the strong CH acid 1-acetylindene by the action of compound (VI) occurs in the presence of a nucleophilic catalyst (Et4NCl).