Synthesis 2003(2): 0213-0216
DOI: 10.1055/s-2003-36820
PAPER
© Georg Thieme Verlag Stuttgart · New York

Improved Solubility of Hypervalent Iodine-Benzyne Precursors: Synthesis and Reaction of (Phenyl)[2-(trimethylsilyl)phenyl]iodonium Salts Bearing Long Alkyl Chains

Tsugio Kitamura*a, Takayoshi Abeb, Yuzo Fujiwarab, Teizo Yamajib
a Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
Fax: +81(952)288550; e-Mail: kitamura@cc.saga-u.ac.jp;
b Department of Applied Chemistry, Faculty of Engineering, Kyushu University, Hakozaki, Fukuoka 812-8581, Japan
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Publikationsverlauf

Received 21 September 2002
Publikationsdatum:
22. Januar 2003 (online)

Abstract

Synthesis of new long-chained hypervalent iodine-benzyne precursors, (4-dodecylphenyl)[2-(trimethylsilyl)phenyl]iodonium triflate and the tetradecyl derivative, is described. The benzyne precursors dissolve even in organic solvents of low polarity such as diethyl ether, THF, cyclopentyl methyl ether, benzene, and toluene. The trapping reactions with furan and tetraphenylcyclopentadienone in the above solvent give the benzyne adducts in high yields without any loss of high reactivity of hypervalent iodine-benzyne precursors.