10-NCCH2CH2OCH2CH2C≡N-7,8-C2B9H11: Synthesis and Reactions with Various Nucleophiles

Stogniy, M.Y.; Erokhina, S.A.; Anisimov, A.A.; Suponitsky, K.Y.; Sivaev, I.B.; Bregadze, V.I.

Авторы: Stogniy Marina Yu, Erokhina Svetlana A., Anisimov Aleksei A., Suponitsky Kirill Yu, Sivaev Igor B., Bregadze Vladimir I.
Журнал: Polyhedron
Том: 174
Год издания: 2019
Издательство: Pergamon Press
Местоположение издательства: United States
Номер статьи: 114170
DOI: 10.1016/j.poly.2019.114170
Аннотация: The 10-(3-cyanoethoxypropionitrilium) derivative of nido-carborane 10-NCCH2CH2OCH2CH2C≡N-7,8-C2B9H11 (1) was prepared by the reaction of the parent nido-carborane [7,8-C2B9H12]- with bis(2-cyanoethyl) ether in the presence of HgCl2. Hydrolysis of 1 produces the corresponding iminol 10-NCCH2CH2OCH2CH2C(OH)=HN-7,8-C2B9H11 (2). Treatment of iminol 2 with triethylamine results in the side chain shortening with formation of the acrylamide derivative 10-CH2=CH-C(=O)HN-7,8-C2B9H11 (3). Reactions of 1 with alcohols produce two main products – imidates derived from 3-hydroxypropionic acid 10-HOCH2CH2C(OR)=HN-7,8-C2B9H11 (R = Me (4), Et (6), iPr (8), Bu (10)) and imidates derived from acrylic acid 10-CH2=CH-C(OR)=HN-7,8-C2B9H11 (R = Me (5), Et (7), iPr (9), Bu (11)). Reactions of 1 with thiols lead to thioimidates with preserved side chain 10-NCCH2CH2OCH2CH2C(SR)=HN-7,8-C2B9H11 (R = Et (12), Bu (13)) as mixtures of E and Z isomers which were separated by column chromatography on silica. The reaction of 1 with diethylamine results in the 3-hydroxypropionic acid derived amidine 10-HOCH2CH2C(NEt2)=HN-7,8-C2B9H11 (14). The crystal molecular structure of imidate 10-CH2=CH-C(OEt)=HN-7,8-C2B9H11 (7) was determined by single crystal X-ray diffraction.
Добавил в систему: Стогний Марина Юрьевна

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10-NCCH2CH2OCH2CH2C≡N-7,8-C2B9H11: Synthesis and Reactions with Various Nucleophilesстатья

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