Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts; European Journal of Organic Chemistry; Vol. 2015, iss. 22
| Parent link: | European Journal of Organic Chemistry Vol. 2015, iss. 22.— 2015.— [P. 4831-4834] |
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| Institution som forfatter: | |
| Andre forfattere: | , , , , , |
| Summary: | 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. |
| Sprog: | engelsk |
| Udgivet: |
2015
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| Fag: | |
| Online adgang: | http://dx.doi.org/10.1002/ejoc.201500535 |
| Format: | MixedMaterials Electronisk Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=644164 |