Pregled bibliografske jedinice broj: 75893
Metalation of 3-trimethylsilyl-3-ethoxycarbonylcyclopropenes derivatives
Metalation of 3-trimethylsilyl-3-ethoxycarbonylcyclopropenes derivatives // 8th European Symposium on Organic Chemistry : ESOR-8 : Programme and Abstracts / Eckert-Maksić, Mirjana ; Glasovac, Zoran ; Zrinski, Irena (ur.).
Zagreb: Institut Ruđer Bošković, 2001. str. 182-182 (poster, međunarodna recenzija, sažetak, znanstveni)
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Naslov
Metalation of 3-trimethylsilyl-3-ethoxycarbonylcyclopropenes derivatives
Autori
Zrinski, Irena ; Eckert-Maksić, Mirjana
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni
Izvornik
8th European Symposium on Organic Chemistry : ESOR-8 : Programme and Abstracts
/ Eckert-Maksić, Mirjana ; Glasovac, Zoran ; Zrinski, Irena - Zagreb : Institut Ruđer Bošković, 2001, 182-182
Skup
European Symposium on Organic Chemistry (8 ; 2001)
Mjesto i datum
Dubrovnik, Hrvatska; Cavtat, Hrvatska, 01.09.2001. - 06.09.2001
Vrsta sudjelovanja
Poster
Vrsta recenzije
Međunarodna recenzija
Ključne riječi
cyclopropene derivatives; metallation reaction; mechanism
Sažetak
In a recent attempt to silylate olefinic position in 3-trimethylsilyl-3-ethoxycarbonylcyclopropene (1) we obtained ethyl 4-mono(trimethylsilyl)-3-butinoate (2) as the only product. The lack of C-silylation was rationalised by involvement of C→ ; O Me_3Si migration in the course of reaction leading to formation of silyl ketene acetal derivative prior to hydrolysis. In this contribution, metallation/silylation reaction of alkyl derivative of 1, exemplified by compound 3, will be discussed. Treatment of 3 with LDA in THF/TMEDA at low temperature (-60 º ; ; C to 0 º ; ; C) in the presence of Me_3SiCl ("in situ") lead to silyl ketene acetal 4, which upon hydrolysis results in a mixture of diastereomeric allenes 5 and 6 (Scheme 1). Mechanism of reaction will be discussed in some detail.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
