Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts
| Parent link: | European Journal of Organic Chemistry Vol. 2015, iss. 22.— 2015.— [P. 4831-4834] |
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| Korporativna značnica: | |
| Drugi avtorji: | , , , , , |
| Izvleček: | Title screen (4-Triisopropylsilylphenyl)phenyliodonium tosylate, an aryliodonium salt bearing an extremely bulky, electron-donating triisopropylsilyl (TIPS) substituent in the phenyl ring, was prepared by the reaction of (4-tributyltinphenyl)triisopropylsilane with [hydroxy(tosyloxy)iodo]benzene (Koser's reagent). The TIPS-substituted aryliodonium tosylate was further converted into (4-triisopropylsilylphenyl)phenyliodonium bromide, the structure of which was established by single-crystal X-ray diffraction. Reactions of the TIPS-substituted arylodonium tosylate with bromide, azide, and thiocyanate anions predominantly afforded products of nucleophilic substitution in the electron-rich aromatic ring bearing the TIPS substituent. This unusual result is explained by the steric effect of the extraordinary bulky para-TIPS substituent on the configuration of the reaction intermediate. |
| Jezik: | angleščina |
| Izdano: |
2015
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| Teme: | |
| Online dostop: | http://dx.doi.org/10.1002/ejoc.201500535 |
| Format: | Elektronski Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=644164 |
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| 200 | 1 | |a Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts |f M. S. Yusubov, D. Yu. Svitich, A. Yoshimura [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: p. 4834 (12 tit.)] | ||
| 330 | |a (4-Triisopropylsilylphenyl)phenyliodonium tosylate, an aryliodonium salt bearing an extremely bulky, electron-donating triisopropylsilyl (TIPS) substituent in the phenyl ring, was prepared by the reaction of (4-tributyltinphenyl)triisopropylsilane with [hydroxy(tosyloxy)iodo]benzene (Koser's reagent). The TIPS-substituted aryliodonium tosylate was further converted into (4-triisopropylsilylphenyl)phenyliodonium bromide, the structure of which was established by single-crystal X-ray diffraction. Reactions of the TIPS-substituted arylodonium tosylate with bromide, azide, and thiocyanate anions predominantly afforded products of nucleophilic substitution in the electron-rich aromatic ring bearing the TIPS substituent. This unusual result is explained by the steric effect of the extraordinary bulky para-TIPS substituent on the configuration of the reaction intermediate. | ||
| 461 | |t European Journal of Organic Chemistry | ||
| 463 | |t Vol. 2015, iss. 22 |v [P. 4831-4834] |d 2015 | ||
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