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Mercuracarborand-catalyzed Diels-Alder reactions of a thionoester with cyclopentadiene

✍ Scribed by Hans Lee; Martin Diaz; M.Frederick Hawthorne

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
302 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The multidentate Lewis acids B-octamethyl [12]-mercuracarborand-4 (1) and B-hexamethyl [9]mercuracarborand-3 (2) catalyze the Diels-Alder reaction of a thionoester 4 with cyclopentadiene. The reaction proceeds more rapidly when catalyzed with 1 and 2 than with monodentate bis(closo-9,12-dimethyl-1,2carboran-1-yl)mercury (3). Mercury-199 NMR studies demonstrated the formation of a 1:1 complex of 1 with 4 in which the thio function of 4 is coordinated to the Hg(II) centers of 1, while the 2.4 and 3-4 complexes are not observed by NMR.

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191 a) Dr. A. Meyer, Stuttgart is thanked for the elemental analyses; b) Gd5CIVC2 is monoclinic, space group P2,/c (No. 14), a=918.2(3), b=1612.0(5), C = 1288.6(4) pm,/3= 119.86(2)"; Z = 4 ; R=0.026 with 3539 reflexions I > 2 a (I).