Abstract
The 10-(3-cyanoethoxypropionitrilium) derivative of nido-carborane 10-NCCH2CH2OCH2CH2CN-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-CH2CH-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-CH2CH-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-CH2CH-C(OEt)HN-7,8-C2B9H11 (7) was determined by single crystal X-ray diffraction.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
