34257-56-2Relevant articles and documents
Oxidation of Alkylthio Substituted Tricarbonyl(η6-arene)chromium(0) Complexes to Alkylsulfinyl Substituted Tricarbonyl(η6-arene)chromium(0) Complexes
Perez-Encabo, Alfonso,Perrio, Stephane,Slawin, Alexandra M. Z.,Thomas, Susan E.,Wierzchleyski, Adam T.,Williams, David J.
, p. 629 - 642 (2007/10/02)
Dimethyldioxirane efficiently oxidises tricarbonylchromium(0) complexes of alkylthio substituted arenes to tricarbonylchromium(0) complexes of alkylsulfinyl substituted arenes.The diastereoselectivity of oxidation of ortho substituted complexes, which was determined by inter alia X-ray crystal structure analyses of tricarbonyl6-1-methoxy-2-(methylsulfinyl)benzene>-chromium(0) 20x, 6-1-(tert-butylsulfinyl)-2-methoxybenzene>tricarbonylchromium(0) 23x and tricarbonyl6-1-(ethylsulfinyl)-2-methoxybenzene)chromium(0) 21y, is dependent on the alkylthio substituent and is reversed when this substituent is changed from methylthio to tert-butylthio.
METALATION REACTIONS. XIV. REGIOSPECIFIC PREPARATION OF POLYSUBSTITUTED BENZENES VIA MONO- OR DI-LITHIATION REACTIONS OF AROMATIC THIOETHERS
Cabiddu, Salvatore,Fattuoni, Claudia,Floris, Costantino,Gelli, Gioanna,Melis, Stefana,Sotgiu, Francesca
, p. 861 - 884 (2007/10/02)
The preparation of polyfunctionalized aromatic thioethers either by one-step dilithiation or by two successive one-flask monometalation reactions is described.By acting on 1 two equal or different electrophiles one on the thiomethyl group and one in the ortho-position with respect to it are introduced; by acting on 11 and on 35 the substitution involves the thiomethyl carbon atom and that in the ortho-position with respect to the alkoxy group.In the case of the homologeous isopropylthio (23) the substitution involves the two aryl carbon atoms in the ortho-position to both functions.In the case of the p-disubstituted isomers (49, 59) analogous behaviour to ortho isomers in one-step metalation reaction is observed, while the two hydrogen atoms in the ortho-positions to the methoxy group are substituted when two successive monometalations are employed.The metalation of 40 results low selective.The behaviour of 79 and 93 is analogous to 1, while 72, 88 and 96 undergo only one-step monometalation reactions.
SELECTIVE CLEAVAGE OF THE CARBON-SULPHUR AND CARBON-OXYGEN BONDS IN METHOXYTHIOANISOLES
Testaferri, L.,Tiecco, M.,Tingoli, M.,Chianelli, D.,Maiolo, F.
, p. 2721 - 2724 (2007/10/02)
Selective cleavage of thioether or ether functions in methoxythioanisoles in hexamehtylphosphoramide (HMPA) with sodium gives methoxythiophenols by cleavage of the carbon-sulphur bond.Reactions with sodium isopropanethiolate give instead the thiomethoxyphenols by dealkylation of the methoxy function.When the methoxythioanisoles were treated first with sodium isopropanethiolate and then with sodium complete dealkylation was achieved with formation of mercaptophenols.The present methods have considerable advantages over existing procedures for the synthesis of methoxythiophenols, thiomethoxyphenols and mercaptophenols.The mechanistic implications of the reactions investigated are also discussed.
