Journal of Organic Chemistry p. 2746 - 2750 (1985)
Update date:2022-08-04
Topics:
Crump, Stephen L.
Netka, Jill
Rickborn, Bruce
A one-pot procedure is described for carrying out the sequence 1,4-elimination of acetal 1 to form isobenzofuran; the formation of 1,3-dilithioisobenzofuran; the conversion to 1,3-bis(trimethylsilyl)isobenzofuran (5); the generation of arynes and cycloaddition to 5.This method allows the use of lithium tetramethylpiperidide induced dehydrohalogenation of haloaromatics to generate the arynes, a procedure which fails with unsilylated isobenzofuran due to the acidity of the 1,3-protons.The protiodesilylation of the cycloadducts occurs with surprising ease, upon treatmentwith either tetraalkylammonium fluoride/THF or base (potassium tert-butoxide or KOH) in Me2SO, to furnish the novel unsubstituted isobenzofuran-aryne adducts.Three examples are given, utilizing benzyne, 1-naphthalyne, and 3-pyridine.Procedures for subsequent deoxygenation of the cycloadducts to anthracene, benzanthracene, and benz
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Doi:10.1139/v64-412
(1964)Doi:10.1002/jlac.198519850502
(1985)Doi:10.1002/hlca.19570400638
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(1985)