Functionalization of polymethylcarboranes. Preparation and reactivity of 2,3,4,5,6,7,8,9,10,11-decamethyl-1,12-dicarba-closo-dodecaborane(12)-1- carboxylic acid

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 5, 1999, Pages 699-701

  Endo, Yasuyuki ^a   Yaguchi, Kyoko ^a   Tsuji, Motonori ^a   Yamaguchi, Kentaro ^b   Shudo, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Acyl chloride; Carboxylation; Dicarba closo dodecaborane; Friedel Crafts reaction; Hydrolysis

Indexed keywords

2,3,4,5,6,7,8,9,10,11 DECAMETHYL 1,12 DICARBA CLOSO DODECABORANE(12) 1 CARBOXYLIC ACID; CARBORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; CRYSTAL STRUCTURE; HYDROGEN BOND; HYDROLYSIS; METHYLATION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032997635     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.699     Document Type: Article

References (10)

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5. Iijima T., Endo Y., Kawachi E., Kagechika H., Shudo K., Chem. Pharm. Bull., 398-404 (1999).
6. Attempts to prepare 3,4,5,6,7,8,9,10,11,12-decamethyl-1,2-dicarba- closo-dodecaborane(12) (o-carborane) or 2,3,4,5,6,8,9,10,11,12-decamethyl-1,7-dicarba-closo-dodecaborane(12) (m-carborane) by the present procedure were unsuccessful.
7. 2O, deuteration of CH was not observed.
8. A facile decarboxylation of 1,2-dicarba-closo-dodecaborane-1-carboxylic acid due to a leaving ability of 1,2-dicarba-closo-dodecaborane has been reported: Nakamura H., Aoyagi, K., Yamamoto, Y., J. Org. Chem., 62, 780-781 (1997). However, the compound 3 was stable under a diluted alkaline condition.
9. w=0.063 for 2090 independent reflections with I>3σ(I). Selected bond length: B1-C range 1.714-1.743 average 1.735, B12-C range 1.692-1.697 average 1.694, B-B range 1.754-1.804 average 1.779, C1-C12 cross cage distance 3.007 Å.
10. Azumaya I., Yamaguchi K., Kagechika H., Saito S., Itai A., Shudo K., Yakugaku Zasshi, 114, 414-430 (1994).