75384-19-9Relevant articles and documents
[3,3]-sigmatropic rearrangement versus carbene formation in gold-catalyzed transformations of alkynyl aryl sulfoxides: Mechanistic studies and expanded reaction scope
Lu, Biao,Li, Yuxue,Wang, Youliang,Aue, Donald H.,Luo, Yingdong,Zhang, Liming
supporting information, p. 8512 - 8524 (2013/07/19)
Gold-catalyzed intramolecular oxidation of terminal alkynes with an arenesulfinyl group as the tethered oxidant is a reaction of high impact in gold chemistry, as it introduced to the field the highly valued concept of gold carbene generation via alkyne o
Preparation and Reactions of Novel Cyclic β-Oxosulphonium Salts obtained by the Acid-induced Cycisation of 1-Diazo-ω-phenylthio-2-alkanones
Flowers, William T.,Freitas, Ana M.,Holt, Geoffrey,Purkiss, Stuart C.
, p. 1119 - 1124 (2007/10/02)
With perchloric acid, the diazo-ketones PhSnCOCHN2 (1a)-(1d) give the corresponding cyclic β-oxosulphonium salts (2a)-(2d); the p-chlorophenyl analogue of (2d) was similarly prepared.The salts (2a), (2c), and (2d) react with triphenylphosphine at C(2) to give the acyclic phosphonium salts (3a), (3c), and (3d) and, analogously, with potassium O-ethyl dithiocarbonate to give the corresponding acyclic O-ethyl dithiocarbonates (3f), (3g), and (3h).All the reactions of the salt (2b) with nucleophiles gave either 1-phenylthiobut-3-en-2-one (11) or products of its Michael addition.Salts (2c) and (2d) with sodium methoxide in methanol provide, respectively, methyl ω-phenylthio-butanoate and -pentanoate in a process that involves the loss of a methylene group.These and other reactions are considered to proceed via ylide intermediates; the intermediate derived by the deprotonation of (2d) being isolated, whereas that from (2c) rearranged to give 3-phenylthiocyclopentanone.
