Novel conversion of aromatic ester groups to methyl. Catalytic effect of iodine in reactions involving iodotrimethylsilane

Trimethylsilyl-based reagents

“…A variety of carboxylic acid esters are smoothly transformed 3 , 4 2 into the corresponding silyl ester (1) on treatment with iodotrimethylsilane (Scheme 18.9). The initial reversible complexation can be catalysed 43 by iodine. The initial reversible complexation can be catalysed 43 by iodine.…”

Silyl phosphites. Part 20. A facile synthesis of phosphoenolpyruvate and its analogue utilizing in situ generated trimethylsilyl bromide

“…The mixture was heated at 150 "C for 1 h after which the lH n.m.r. spectrum of the mixture indicated the absence of compound (23) and the formation of compound ( 8 ) . Distillation of the reaction mixture gave the latter (13.3 g, 71y0), b.p.…”

Catalyst-free depolymerization of polycaprolactone to silylated monoesters and iodide derivatives using iodosilanes

“…This reaction is reminiscent of the reduction of aromatic acids and aromatic silylesters into benzylic trichlorosilanes (ArCH 2 SiCl 3 ) by HSiCl 3 . 37 Compounds 1-6 are relevant molecules in organic chemistry and in materials science. Silyl esters are indeed convenient intermediates for the preparation of functional polymeric substrates such as easily degradable poly(silylester)s and extensively used as biodegradable surgical devices, matrices for drug delivery, etc.…”

“…This reaction is reminiscent of the reduction of aromatic acids and aromatic silylesters into benzylic trichlorosilanes (ArCH 2 SiCl 3 ) by HSiCl 3 . 37…”