Metalation of 3-trimethylsilyl-3-ethoxycarbonylcyclopropenes derivatives (CROSBI ID 482745)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija
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 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.
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