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Thia-Fries rearrangements

Keywords aryl sulfonate, microwave irradiation, thia-Fries rearrangement, 2-ar-ylsulfonyl phenol... [Pg.378]

Treatment of (9-arylsulfonate esters with AICI3—ZnCl2, on sihca with micro-wave irradiation, leads to 2-sulfonyl phenols in a thia-Fries rearrangement. A similar reaction was reported with (9-arylsulfonamides. ... [Pg.737]

Charmant, J. P. H., Dyke, A. M., Lloyd-Jones, G. C. The anionic thia-Fries rearrangement of aryl triflates. Chem. Common. 2003, 380-381. Mouhtady, O., Gaspard-lloughmane, H., Roques, N., Le Roux, C. Metal triflates-methanesulfonic acid as new catalytic systems application to the Fries rearrangement. Tetrahedron Lett. 2003,44, 6379-6382. [Pg.591]

The so-called thia-Fries rearrangement occurs upon treatment of aryl phenylsulfinates 235 (obtained by reaction of phenols with phenylsulfinyl chloride) with AICI3 at 25 °C to afford the (phenylsulfinyl)phenols 236 in good yields (equation 107) . [Pg.776]

Thia-Fries rearrangement Benzenesulfinylphenols are obtained on treatment of the aryl benzenesulfinates with AICI3 in CH Cl at room temperature. [Pg.12]

Example 6, Remote Anionic Thia-Fries rearrangement ... [Pg.267]

An unusual sodium hydride-mediated remote anionic 1,5-thia-Fries rearrangement reaction was developed by Xu and eoworkers recently [82]. Their method provides an effieient approach for the regioseleetive synthesis of not only 2-(2-hydroxyphenyl)-3-indole triflones but also the related 3-sulfonylindoles (164 165) (Figure 18.10) [82]. [Pg.505]

Thia-Fries rearrangement of aryl sulfonates under microwave irridiation... [Pg.506]

A 2-phosphinoxido-2 -alkanesulfonyl-binaphthyl was subjected to deoxygenation using trichlorosilane and the so-formed intermediate underwent a lithium diisopropylamide-mediated thia-Fries rearrangement to provide the enantiomerically pure 2-phosphino-2 -hydroxy-3 -alkanesulfo-nyl-binaphthyl (Scheme 43). ... [Pg.87]

Ring expansion of keto aziridines to the 2,5-diaryloxazoles in the presence of dicyclohexyl carbodiimide and iodine has been reported. A tandem thia-Fries rearrangement of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate aryne precursors has been described (Scheme 76). ° ... [Pg.549]

SCHEME 73 Thia-Fries rearrangement involving arynes to form phenoxathiin-dioxide [100]. [Pg.70]

C. HaU, J.L. Henderson, G. Emouf, M.F. Greaney, Tandem thia-Fries rearrangement-cycHsation of 2-(trimethylsilyl)phenyl trifluorometh-anesulfonate benzyne precursors, Chem. Commun. 49 (2013) 7602-7604. [Pg.76]

It has been reported that (phenyl triflate)chromium complexes, even if electron rich, have a propensity to undergo anionic thia-Fries rearrangements in preference to triflate elimination (Scheme 99). ... [Pg.502]

An AlCl3-ZnCl2 mixture supported on silica gel was found to be a newer and efficient medium for the thia-Fries rearrangement of aryl sulfonates in solvent-free conditions under microwave dielectric heating (Moghaddam and Dakamin, 2000). [Pg.220]

See other pages where Thia-Fries rearrangements is mentioned: [Pg.194]    [Pg.1109]    [Pg.380]    [Pg.1144]    [Pg.241]    [Pg.267]    [Pg.509]    [Pg.56]    [Pg.587]    [Pg.509]    [Pg.70]    [Pg.241]    [Pg.208]   
See also in sourсe #XX -- [ Pg.194 ]

See also in sourсe #XX -- [ Pg.12 ]

See also in sourсe #XX -- [ Pg.380 ]

See also in sourсe #XX -- [ Pg.241 ]

See also in sourсe #XX -- [ Pg.241 ]

See also in sourсe #XX -- [ Pg.505 ]

See also in sourсe #XX -- [ Pg.549 , Pg.587 ]

See also in sourсe #XX -- [ Pg.241 ]



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