Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryl­iodonium Salts

Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryl­iodonium Salts

מידע ביבליוגרפי
Parent link:European Journal of Organic Chemistry
Vol. 2015, iss. 22.— 2015.— [P. 4831-4834]
מחבר תאגידי: Национальный исследовательский Томский политехнический университет (ТПУ) Институт природных ресурсов (ИПР) Кафедра технологии органических веществ и полимерных материалов (ТОВПМ)
מחברים אחרים: Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich), Svitich D. Yu. Dmitry Yurjevich, Yoshimura A. Akira, Kaster B. J. Brent, Nemykin V. N. Viktor Nikolaevich, Zhdankin V. V. Viktor Vladimirovich
סיכום: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.
יצא לאור: 2015
נושאים:
электронный ресурс
труды учёных ТПУ
hypervalent compounds
iodine
silicon
גישה מקוונת:http://dx.doi.org/10.1002/ejoc.201500535
פורמט: אלקטרוני Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=644164
תיאור
סיכום: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.
DOI:10.1002/ejoc.201500535

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