64741-11-3Relevant academic research and scientific papers
Ruthenium-catalyzed reaction of alkenyl triflates with zinc thiolates
Imazaki, Yusuke,Shirakawa, Eiji,Hayashi, Tamio
experimental part, p. 10212 - 10215 (2012/01/05)
A ruthenium complex coordinated with 3,4,7,8-tetramethyl-1,10- phenanthroline catalyzed the reaction of alkenyl triflates with zinc dithiolates to give alkenyl sulfides.
Improved and environmentally friendly large-scale preparation of cyclohexadienyl-, cycloheptadienyl sulfone and enantiopure epoxy cycloheptyl sulfones
Park, Taesik,Torres, Eduardo,Fuchs, Philip L.
, p. 1895 - 1900 (2007/10/03)
Kilogram-scale amounts of cycloheptadienyl phenylsulfone and cyclohexadienyl phenylsulfone were prepared by one operation in 5 stages with over 50% yield and requiring no purification. A practical and efficient method for the Jacobsen asymmetric epoxidati
Mono- and bisadducts from the addition of thianthrene cation radical salts to cycloalkenes and alkenes
Qian, Ding-Quan,Shine, Henry J.,Guzman-Jimenez, Ilse Y.,Thurston, John H.,Whitmire, Kenton H.
, p. 4030 - 4039 (2007/10/03)
Thianthrene cation radical salts, Th.+ X-(X- = a, ClO4-; b, PF6-; c, SbF6-), add to cycloalkenes (C5-C8) in acetonitrile (MeCN) to form 1,2-bis(5-thianthreniumyl)cycloalkane salts and 1,2-(5,10-thianthreniumdiyl)cycloalkane salts, most of which have now been isolated and characterized. These are called bis- (3, 6, 9, 12) and monoadducts (4, 7, 10, 13). The proportional amount of the monoadduct obtained in the initial stage of the reaction varied with the cycloalkene in the order C6 ? C5 7 ? C8. Thus, the ratio bis:mono for C5 and C7 was, respectively, about 80/20 and 50/50. In contrast, only about 5% of the C6 monoadduct (7a) and none of 7b, c was obtained, while for C8 none of the bisadducts 12a-c was found. Bisadducts 3 and 9 lost thianthrene (Th) slowly in MeCN solution and changed into monoadducts 4 and 10. A comparable change from 6a into 7a was not observed. The monoadducts, themselves, lost a proton slowly in dry MeCN and opened into 1-(5-thianthreniumyl)cycloalkenes (5, 8, 11, 14). With 3 and 9, particularly, it was possible to follow with NMR spectroscopy the succession of changes, for example, 3 to 4 to 5. The opening of a monoadduct was made faster by adding a small amount of water to the solution. The bisadducts of 4-methylcyclohexene (15a) and 1,5- cyclooctadiene (17a) were isolated and characterized. Although a small amount of monodduct (16a) of 4-methylcyclohexene was found with NMR spectroscopy, it could not be isolated. Bis- and monoadducts were obtained also in additions of Th.+ ClO4- to acyclic alkenes, in relative amounts that, again, varied with the alkene. From cis-2-butene the dominant product was the bisadduct (18), while the monoaduct (19) was characterized with NMR spectroscopy but could not be isolated. In contrast, trans-3-hexene gave mainly the monoadduct (21), while the bis adduct (20) could not be isolated. With 4-methyl-cis-2-pentene, both bis- (22) and monoadduct (23) were isolated, the former being dominant. The conversion of 18 into 19 was characterized with NMR spectroscopy. In all cycloalkene bisadducts, the configurational relationship of the two thianthrenium groups was trans, while in the monoadducts, the bonds to the single thianthrene dication were (necessarily) cis. In both bis- and monoadducts of acyclic alkenes, the configuration of the alkene was retained. The mechanisms of addition with retention of configuration, of conversion of a bis- into a monoadduct, and of opening of a monoadduct are discussed. Products were identified with a combination of NMR spectroscopy, X-ray crystallography, elemental analysis, and (for cycloalkene adducts) reaction with thiophenoxide ion.
Economical and environmentally friendly syntheses of 2-(phenylsulfonyl)-1,3-cyclohexadiene and 2-(phenylsulfonyl)-1,3-cycloheptadiene
Meyers, David J.,Fuchs, Philip L.
, p. 200 - 204 (2007/10/03)
A large-scale and inexpensive synthesis of dienes 1 and 2 has been developed via a four-step procedure starting with benzenethiol and the corresponding cyclic ketone. No chromatography is required.
A Simple Method for Producing Cycloalkenyllithiums from Cycloalkanones via Reductive Lithiation of Enol Phenyl Thioethers
Cohen, Theodore,Doubleday, Mary Dosch
, p. 4784 - 4786 (2007/10/02)
Cyclohexenyl, cycloheptenyl, and cyclooctenyl phenyl sulfides, readily prepared from the corresponding cycloalkanones, are reductively lithiated by lithium p,p'-di-tert-butylbiphenylide to produce cycloalkenyllithiums in good yields.
Clay Catalysis: A Simple and Efficient Synthesis of Enolthioethers from Cyclic Ketones
Labiad, Bouchta,Villemin, Didier
, p. 143 - 144 (2007/10/02)
Montmorillonite KSF in refluxing toluene catalyses the synthesis of 1-alkyl- and 1-arylthioalkenes from ketones and thiols (thiophenol or 1-butanethiol).
A New Syntethic Route to Vinyl Sulfides Utilizing the Reaction of (Phenylthio)carbenes with Nitrile Anions
Harada, Toshiro,Karasawa, Akio,Oku, Akira
, p. 842 - 846 (2007/10/02)
Reactions of nitrile anion (LiCR2R3CN) and (phenylthio)carbenes generated from 1-chloroalkyl phenyl sulfides (R1CH(Cl)SPh) 2a-e by the action of n-BuLi have been shown to be a useful synthetic route to vinyl sulfides (PhSC(R1)=CR2R3) 3a-k (34-91percent).The nucleophilic attack of the nitrile anion on the carbenic species gave the presumed intermediate β-(phenylthio)-β-lithionitrile, which eliminated LiCN to give the expected vinyl sulfides.The application of the present reaction to the synthesis of cyclic vinyl sulfides was successful: the decomposition of the dianion ofω,ω-bis(phenylthio)alkanenitriles (8b, 8c, 11, and 14) affording the corresponding 1-(phenylthio)cycloalkenes (9, 10, 12, and 15) in 12-87percent yields.
A SIMPLE SYNTHESIS OF SOME CYCLIC AND ACYCLIC CYCLOBUTENEDIONES
Liebeskind, Lanny S.,Baysdon, Sherrol L.
, p. 1747 - 1750 (2007/10/02)
Cyclobutenediones can be prepared from cyclic and acyclic ketones by a simple four step procedure.
