Rearrangement on protonation of the 7,9-dimethyl-8-benzyl-7,9-dicarbanido-undecaborate anion into 2,7-dimethyl 11-benzyl-2,7-dicarba-nido-undecaborane(13)

Zakharkin, L. I.; Zhigareva, G. G.; Antonovich, V. A.; Yanovskii, A. I.; Struchkov, Yu. T.

doi:10.1007/bf00956555

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“…[20][21][22] The alkylations have been shown to proceed via cage isomers 11-R-2,7-nido-C 2 B 9 H 11 − , one of which (R = Me) could be isolated as a protonated species. 21,[23][24][25] 27,28 Herein, we demonstrate that sulfenyl chlorides also may act as appropriate reagents in electrophilic substitutions with 1 and give the expected asymmetric products in high yield.…”

Section: Introductionmentioning

confidence: 99%

Electrophilic substitution of the nido-dicarbaborate anion 7,8-nido-C2B9H12− with sulfenyl chlorides

et al. 2012

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Sulfenyl chlorides RSCl (R = p-C(6)H(4)OMe, Ph, p-C(6)H(4)NO(2), CN or 2-C(5)H(4)N) react with 7,8-nido-C(2)B(9)H(12)(-) with asymmetric substitution on the pentagonal C(2)B(3) face to give 9-RS-7,8-nido-C(2)B(9)H(11)(-) (R = p-C(6)H(4)OMe (3), Ph (4), p-C(6)H(4)NO(2) (5), CN (6)) and the zwitterion 9-(S-2-C(5)H(4)NH)-7,8-nido-C(2)B(9)H(11) (7), respectively, in high yield, while tBuSCl did not react and S(2)Cl(2) led to decomposition. Further reaction of 5-7 with iodine gave the corresponding iodo derivatives NMe(4) [9-I-11-RS-7,8-nido-C(2)B(9)H(10)] (R = p-C(6)H(4)NO(2) (8), CN (9)) and the zwitterion 9-I-11-(S-2-C(5)H(4)NH)-7,8-nido-C(2)B(9)H(11) (10), respectively. Compounds 3-10 were fully characterised by (1)H, (11)B, (11)B{(1)H}, (13)C{(1)H} spectroscopy, IR spectroscopy, mass spectrometry and elemental analysis, 3-7 also by (11)B-(11)B{(1)H} COSY NMR spectroscopy and 8-10 by X-ray structure determination.

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Section: Introductionmentioning

confidence: 99%

Electrophilic substitution of the nido-dicarbaborate anion 7,8-nido-C2B9H12− with sulfenyl chlorides

et al. 2012

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“…12-14 For example, [3,3,3 ] and 2,9-C 2 B 9 H 13 respectively. 12, 13 We were attracted to the neutral B-methylated carborane 11-Me-2,7-C 2 B 9 H 12 4, [15][16][17][18] prepared from the reaction of nido-7,8-C 2 B 9 H 11 2Ϫ with MeI followed by acidification. The carborane can lead to three isomeric B-methylated nido carborane anions MeC 2 B 9 H 11 Ϫ on deprotonation.…”

Section: Introductionmentioning

confidence: 99%

“…The carborane can lead to three isomeric B-methylated nido carborane anions MeC 2 B 9 H 11 Ϫ on deprotonation. 15,16 As shown in Scheme 1, the double deprotonation of 4 with two equivalents of a strong † Electronic supplementary information (ESI) available: rotatable 3…”

Section: Introductionmentioning

confidence: 99%