Reactions of trimethylsilyl-derived iodohydrins with electron-rich π-systemsElectronic supplementary information (ESI) available: Additional results and experimental data, 1H NMR, 13C NMR and mass spectral data. See http://www.rsc.org/suppdata/p1/b1/b105233k

Autor:	Ben-Ami Feit, Sarit Shamai, Eti Ishai
Rok vydání:	2002
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Trimethylsilyl Yield (chemistry) Condensation Acetal Enol ether Organic chemistry Lewis acids and bases Electron Medicinal chemistry Alkyl
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :434-438
ISSN:	1364-5463 1472-7781
DOI:	10.1039/b105233k
Popis:	Reactions of trimethylsilyl-derived iodohydrins of the type R1R2CH–CH(I)OTMS, with electron-rich olefins, and the effects of certain factors on these reactions, were studied. The trimethylsilyl-derived iodohydrins were obtained in situ by reacting R1R2CH–CHO (R1 = R2 = H; R1 = H, R2 = alkyl, phenyl) with TMSI. The corresponding trimethylsilyl enol ether derivatives (R1R2CCH–OTMS), and 1,1-diarylethylenes were the olefins used. Aldehydes of the type RCH2–CHO reacted smoothly in the presence of TMSI to yield the condensation product RCH2–CHC(R)–CHO. Both RCH(–CHCAr2)2 and the cyclic acetal 5 were obtained as main products of the RCHO–TMSI–CH2CAr2 reaction system, depending on the [RCHO] ∶ [TMSI] ∶ [CH2CAr2] concentration ratio. The mechanisms of formation for the various main products and by-products are discussed. TMSI substitutes, formed by reacting Me3SiCl with each of several Lewis acids, were also used.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4ba93a3545c93b90ed5f6e1274697eaa https://doi.org/10.1039/b105233k Zobrazit plný text záznamu