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Allyltrimethylsilane is involved as a reactant in Hosomi Sakurai reaction for allylation in the presence of Lewis acid. For example, it reacts with cyclohexanone to get 1-allylcyclohexanol. It acts as a nucleophile and is involved in Carbon-Ferrier rearrangement.
Reactions with electrophiles illustrate the ß-effect (see Appendix 4); e.g. acid chlorides with a Lewis acid give allyl ketones: J. Organomet. Chem., 85, 149 (1975):
Similarly, carbonyl compounds are converted to homoallylic alcohols: J. Organomet. Chem., 69, C15 (1974). In the TiCl4 promoted reaction with enones, behaves as an allyl anion equivalent, giving the product of conjugate addition (Hosomi-Sakurai reaction): J. Am. Chem. Soc., 99, 1673 (1977); 105, 2354 (1983); Org. Synth. Coll., 7, 443 (1990):
More recent studies have shown that TMS cyclopentanes are also formed in these reactions via a competing [3+2] cycloaddition mechanism: Tetrahedron, 49, 9955 (1993). Chemoselective addition to aldehydes can be accomplished in the presence of a ketone, using Scandium(III) trifluoromethanesulfonate hydrate, 40566 as catalyst: Synthesis, 1822 (1998).
In the presence of F-, functions as an allyl anion equivalent, affording homoallylic alcohols from carbonyl compounds: Tetrahedron Lett., 3043 (1978), and adding to a variety of Michael acceptors: Tetrahedron Lett., 25, 3213 (1984); J. Org. Chem., 51, 1745 (1986). For a review of reactivity in the presence of Lewis acids and F-, see: J. Prakt. Chem./ Chem. Ztg., 336, 375 (1994).
Has also been used, in the presence of a catalyst such as p-TsOH, I2, Br2 or TfOH, as a silylating agent for alcohols, phenols and carboxylic acids: Tetrahedron Lett., 21, 835 (1980); J. Org. Chem., 46, 5212 (1981). The advantage over more conventional silylation methods is that the only by-product is the neutral gas propene.
Srinivas, B.; Reddy, T. R.; Kashyap, S. Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals. Carbohydr Res. 2015, 406, 86-92.
Jayaraman, A.; Jacob, T. V.; Bisskey, J.; Sterenberg, B. T. Sequential electrophilic P-C bond formation in metal-coordinated chlorophosphines. Dalton Trans. 2015, 44 (19), 8788-8791.
Indicaciones de peligro (UE): H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Indicaciones de precaución: P260-P201-P280a-P304+P340-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves and eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.