13522-48-0Relevant academic research and scientific papers
Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
Kearney, Aoife M.,Murphy, Linda,Murphy, Chloe C.,Eccles, Kevin S.,Lawrence, Simon E.,Collins, Stuart G.,Maguire, Anita R.
, (2021/05/04)
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.
NUCLEOPHILIC SUBSTITUTION OF α-HALO-KETONES-XXII ACETOLYSIS OF α'-PHENOXY-α-CHLORO-KETONES. A COMPARISON OF THEIR REACTIVITY WITH THAT OF THE CORRESPONDING THIOETHERS
Pusino, A.,Rosnati, V.,Saba, A.
, p. 1893 - 1900 (2007/10/02)
The results obtained in the acetolysis of α-chloro-ketones 1 a-e are compared with those previously reported for the acetolysis of the corresponding α'-phenylthio-α-chloro-ketones 15a-e and discussed in terms of the enolization-solvolysis mechanisms.
NEW ACETYLENIC MICHAEL RECEPTOR EQUIVALENTS. PART I : SYNTHESIS OF α-SULFENYL - AND α-SULFINYL ACRYLIC DERIVATIVES.
Leyendecker, Francois,Comte, Marie-Therese
, p. 5031 - 5034 (2007/10/02)
The synthesis of α-thioarylated β-unsubstituted acrilic derivatives is reported.
Reactions of 3-(Phenylthio)-3-buten-2-one with Cycloalkanones. A New Approach to Fused Phenols
Takaki, Ken,Okada, Michikazu,Yamada, Michio,Negoro, Kenji
, p. 1200 - 1205 (2007/10/02)
Synthesis and properties of 3-(phenylthio)-3-buten-2-one (7) have been described.The butenone 7 reacted with lithium cycloalkanone enolates to give ketols 14 or diketones 15 in good yields, which were easily transformed into fused phenols 17 by the treatment with p-toluenesulfonic acid or sodium ethoxide, respectively.Oxidative elimination of the sulfenyl group of 14a afforded also 2-naphthol 17a.Tetrahydronaphthalene 23, a key intermediate of calamenene 1a and calamenenal 1b, was successfully synthesized by this approach by starting from l-carvone (19).Bicyclooctanone 25 was obtained in the reaction of 7 with kinetic enolate of 2-cyclohexen-1-one in 84percent yield.
NUCLEOPHILIC SUBSTITUTION OF α-HALO KETONES. XXI. STRUCTURE-REACTIVITY RELATIONSHIPS IN THE ACETOLYSIS OF 3-SUBSTITUTED 1-CHLORO-3-PHENYLTHIO-2-PROPANONES
Pusino, Alba,Rosnati, Vittorio,Saba, Antonio,Franco, Andrea
, p. 475 - 482 (2007/10/02)
The acetolyses of α-chloro ketones 1a-d have been re-investigated under standard conditions and compared with those of the corresponding isomeric substrates 2a-d.It has been shown that participation by the neighbouring phenylthio group, involving a 1-3 shift of the latter, does occur in part even in the case of 1d, while it is the only process in the case of 1e.A few structure-reactivity relationships in the two series of substrates are discussed.
Annelation Reactions of 3-Phenylthiobut-3-en-2-one. A New Method of Constructing Fused Phenols
Takaki, Ken,Okada, Michikazu,Yamada, Michio,Negoro, Kenji
, p. 1183 - 1184 (2007/10/02)
Reactions of 3-phenylthiobut-3-en-2-one with enolate anions of cyclohexanone and cyclopentanone gave good yields of 8a-hydroxy-3-phenylthio-2-decalone and 3a-hydroxy-6-phenylthiohexahydroindan-5-one which were readily converted into 5,6,7,8-tetrahydro-2-naphthol and indan-5-ol, respectively, on exposure to toluene-p-sulphonic acid: a similar reaction of the enolate of cycloheptanone and subsequent treatment with sodium ethoxide gave 2-hydroxy-5,6,7,8-tetrahydrobenzocycloheptene.
