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A facile, efficient, and gram-scale method for the conversion of para-anisic acid into 3,4,5-triiodoanisole through a one-pot C-H iodination/ ipso-iododecarboxylation reaction was investigated. Commercially available benzoic acid was used, which allowed the reaction to be performed on a multigram scale in good yield. This report discloses a practical method for the one-pot synthesis of hitherto unknown 3,4,5-triiodoanisole that is catalytic, scalable, efficient, and easy to work up and purify. Potential application of the target compound as a precursor for novel site-selective metal-iodine exchange and Suzuki-Miyaura cross-coupling reactions were also explored. 3,4,5-Trisubstituted anisole derivatives were provided in a highly regioselective fashion; these compounds are useful building blocks in synthesis and indeed are hard to prepare by any other means. [ABSTRACT FROM AUTHOR]

A general, robust, and efficient method for the conversion of benzoic acids to 1,2,3-triiodoarenes and 1,2,3-trihaloarenes via a two-step synthesis is reported. Commercially available benzoic acids were used that can allow the reactions to be performed on multi-gram scales with good-to-excellent yields. This report discloses a practical method for the synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, scalable, and easy to workup and purify. A potential application of the target compounds as precursors for novel regioselective metal-iodine exchange reaction of 1,2,3-triiodoarenes was also demonstrated. It provided ortho-diiodoaryl derivatives in a high regioselective fashion that are useful intermediates in synthesis and indeed are hard to synthesize by any other means. [ABSTRACT FROM AUTHOR]

Copyright of Canadian Journal of Chemistry is the property of Canadian Science Publishing and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

The article provides information on a study which examined the structure of 2-Propynyl 2,3,4,6-tetra-O-acetyl-&alph-D-mannopyranoside. The study found that with the acetylenic group gauche with respect to position C1, the 2-propynil group in the title compound adopts an exoanomeric conformation. The 13C NMR chemical shifts has been compared with solution and the solid state. The results of the comparison suggests that the acetylenic group also adopts a conformation anti to C1 in solution.

Two new efficient routes for the synthesis of pentaerythritol monobenzyl ether are described. In one route, the known mono‐ O ‐benzylidenepentaerythritol ( 5 ) is selectively benzylated via its dibutylstannylene acetal and then the benzylidene acetal is hydrolized. In the other route, compound 5 is reduced directly to the monobenzyl ether using EtAlCl 2 ‐Et 3 SiH. [ABSTRACT FROM AUTHOR]

Copyright of Canadian Journal of Chemistry is the property of Canadian Science Publishing and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Copyright of Canadian Journal of Chemistry is the property of Canadian Science Publishing and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)