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Synthesis 2003(2): 0213-0216
DOI: 10.1055/s-2003-36820
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
Further Information
Received
21 September 2002
Publication Date:
22 January 2003 (online)
Publication History
Publication Date:
22 January 2003 (online)
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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.
Key words
hypervalent iodine - benzyne - cycloaddition - high solubility - less polar solvent
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