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Metalation of 3-trimethylsilyl-3-ethoxycarbonylcyclopropenes derivatives (CROSBI ID 482745)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Zrinski, Irena ; Eckert-Maksić, Mirjana 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

Podaci o odgovornosti

Zrinski, Irena ; Eckert-Maksić, Mirjana

engleski

Metalation of 3-trimethylsilyl-3-ethoxycarbonylcyclopropenes derivatives

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 &ordm ; ; C to 0 &ordm ; ; 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.

cyclopropene derivatives; metallation reaction; mechanism

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Podaci o prilogu

182-182.

2001.

objavljeno

Podaci o matičnoj publikaciji

8th European Symposium on Organic Chemistry : ESOR-8 : Programme and Abstracts

Eckert-Maksić, Mirjana ; Glasovac, Zoran ; Zrinski, Irena

Zagreb: Institut Ruđer Bošković

Podaci o skupu

European Symposium on Organic Chemistry (8 ; 2001)

poster

01.09.2001-06.09.2001

Dubrovnik, Hrvatska; Cavtat, Hrvatska

Povezanost rada

Kemija