52190-41-7Relevant academic research and scientific papers
Disulfide-based metal-free α-sulfanylation of ketones
Vaquer, Andrea F.,Frongia, Angelo,Secci, Francesco,Tuveri, Enrica
, p. 96695 - 96704 (2015/11/24)
An eco-friendly methodology for the direct α-sulfanylation of ketones, has been developed. The procedure, based on the use of functionalized diaryldisulfides and catalyzed by d,l-proline, represents a mild and efficient approach for the preparation of α-arylthio-ketones.
The effects of C-S and C-Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates
Yoshikawa, Takashi,Mori, Seiji,Shindo, Mitsuru
experimental part, p. 8832 - 8838 (2010/04/06)
Highly Z-selective olefination of acyclic α-thio and α-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the β-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the σ orbital of the C-S bond or a lone pair orbital on the S and σ* orbitals of the breaking C-O bond, and the σ orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the σ* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown.
Efficient and stereoselective synthesis of bicyclo[3.2.1]octan-8-ones: Synthesis and palladium-catalyzed isomerization of functionalized 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans
Langer, Peter,Holtz, Edith,Saleh, Nehad N. R.
, p. 917 - 928 (2007/10/03)
A new C,O-cyclodialkylation of dilithiated cyclic β-keto esters and β-keto sulfones with 1,4-dibromo-2-butene is reported which results in regio- and diastereoselective formation of 2-vinyl-2,3,3a,4,5,6-hexahydro-2,3-benzofurans. The products could be eff
A new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine, and its optically active version
Tanaka,Azuma,Fang,Uchida,Iwata,Ishida,In,Maezaki
, p. 33 - 36 (2007/10/03)
We have developed a new sulfenylation reagent, 3-phenylsulfenyl-2-(N- cyanoimino)thiazolidine 3, that is readily available and stable upon storage. Compound 3 easily reacts with amines or thiols to give the corresponding sulfenamides or asymmetrical disulfides in excellent yields. It was also found that the α-sulfenylation reaction of carbonyl compounds with 3 proceeds smoothly. Furthermore, optically active 4-diphenylmethyl derivative 4 was synthesized as an asymmetric sulfenylation reagent, which realized 96% e.e. upon α-sulfenylation of a cyclic β-keto ester.
New Mild Methodology for the Synthesis of α-Phenylthio and α-Phenylseleno Ketones
Magnus, Philip,Rigollier, Pascal
, p. 6111 - 6114 (2007/10/02)
Treatment of trimethylsilyl enol ethers with the adduct 1, derived from chloramine-T and (PhS)2, gave good yields of α-phenylthioketones.The selenium version of this reagent 2 gave α-phenylselenoketones.
Synthesis of Cyclic Allylic Sulphides (Ring Sizes 5-15) via Phenylthio Participation
Hannaby, Malcolm,Warren, Stuart
, p. 303 - 311 (2007/10/02)
Dehydration of β-phenylthio alcohols occurs with PhS participation unless stereochemistry prevents it.Without PhS participation, mixtures of allylic and vinylic sulphides are formed, but with PhS participation routes to three families of cyclic allylic su
A Ring Expansion of Cyclic Ketones to α-Phenylthio Ketones via Lewis Acid Mediated Denitration
Kim, Sunggak,Park, Jung Ho
, p. 1323 - 1324 (2007/10/02)
The adducts of cyclic ketones with the lithium derivative of (phenylthio)nitromethane are readily rearranged to the ring expanded α-phenylthio ketones via aluminium chloride mediated denitration.
CARBENOID TYPE BASE INDUCED RING EXPANSION OF THE ADDUCTS OF CYCLIC KETONES WITH BIS(PHENYLTHIO)METHYLLITHIUM
Abraham, William D.,Bhupathy, M.,Cohen, Theodore
, p. 2203 - 2206 (2007/10/02)
In another application of the principle that metallo derivatives of bis(phenylthio)acetals behave as carbenoids when present in the same molecule with another anionic group, the adducts of cyclic ketones with bis(phenylthio)methyllithium react with an alk
REARRANGEMENT OF CYCLIC ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS-) GROUP: MIGRATION OF A PhS GROUP AROUND A RING.
Hannaby, Malcolm,Warren, Stuart
, p. 765 - 768 (2007/10/02)
PhS migratoin around rings (size 5-15) gives allyl sulphides with a regioselectivity wich varies with ring size.
REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)KETONES VIA RHODIUM(II) ACETATE CATALYSED ADDITION OF THIOPHENOL TO α-DIAZOKETONES
McKervey, M. Anthony,Ratananukul, Piniti
, p. 2509 - 2512 (2007/10/02)
αα-Addition of thiophenol to α-diazoketones is catalysed efficiently by rhodium(II) acetate in benzene solution at room temperature, offering a convenient regiospecific route to a variety of α-(phenylthio)ketones.
