We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts.
- Authors
Yusubov, Mekhman S.; Svitich, Dmitrii Yu.; Yoshimura, Akira; Kastern, Brent J.; Nemykin, Victor N.; Zhdankin, Viktor V.
- Abstract
(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.
- Subjects
ORGANIC synthesis; IODONIUM salts; AROMATIC compounds; SILYL group; PHENYL group; ANIONS; X-ray diffraction; NUCLEOPHILIC substitution reactions
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 22, p4831
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500535