Издательство СО РАН

Издательство СО РАН

Адрес Издательства СО РАН: Россия, 630090, а/я 187
Новосибирск, Морской пр., 2

soran2.gif

Baner_Nauka_Sibiri.jpg


Яндекс.Метрика

Array
(
    [SESS_AUTH] => Array
        (
            [POLICY] => Array
                (
                    [SESSION_TIMEOUT] => 24
                    [SESSION_IP_MASK] => 0.0.0.0
                    [MAX_STORE_NUM] => 10
                    [STORE_IP_MASK] => 0.0.0.0
                    [STORE_TIMEOUT] => 525600
                    [CHECKWORD_TIMEOUT] => 525600
                    [PASSWORD_LENGTH] => 6
                    [PASSWORD_UPPERCASE] => N
                    [PASSWORD_LOWERCASE] => N
                    [PASSWORD_DIGITS] => N
                    [PASSWORD_PUNCTUATION] => N
                    [LOGIN_ATTEMPTS] => 0
                    [PASSWORD_REQUIREMENTS] => Пароль должен быть не менее 6 символов длиной.
                )

        )

    [SESS_IP] => 44.222.169.36
    [SESS_TIME] => 1711709926
    [BX_SESSION_SIGN] => 9b3eeb12a31176bf2731c6c072271eb6
    [fixed_session_id] => e76b217c97b986f44c9576d0cb8f045d
    [UNIQUE_KEY] => 777d709bd6d56a14f8321334c6eab063
    [BX_LOGIN_NEED_CAPTCHA_LOGIN] => Array
        (
            [LOGIN] => 
            [POLICY_ATTEMPTS] => 0
        )

)

Поиск по журналу

Журнал структурной химии

2010 год, номер 2

Сharacterization and stereochemistry of alkyl 2-chloro- 3-formylacrylates: experimental NMR and theoretical DFT studies

T.M. Barhoumi-slimi, M.T. Ben dhia, M. Nsangou, M.M. El gaied, M.R. Khaddar
Ключевые слова: synthesis, Vilsmeier reaction, stereoisomerism, stereoselectivity, cyclization, NMR, NOEDIFF, B3LYP
Страницы: 266-271

Аннотация

The synthesis of alkyl 2-chloro-3-formylacrylates 1 from alkyl pyruvates was carried out using Vilsmeier reaction. The reaction is highly stereoselective and leads to a 95:5 mixture of <i>Z</i> and <i>E</i> stereoisomers. Both stereoisomers were characterized by <sup>1</sup>H and <sup>13</sup>C NMR. In CDCl<sub>3</sub> solution, the NMR data, particularly the NOEDIFF experiments, show that the major species formed is the <i>Z</i> stereoisomer. Heating compound 1 in THF at reflux afforded the cyclic product 2 in 90 % yield. The interpretation of the experimental data were further supported by DFT/B3LYP calculations.