- Hetarenesulfenyl(Selenyl) Chlorination of (+)-Camphene
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Novel S- and Se-containing terpenoids were prepared by reacting (+)-camphene with N-heterocyclic selenyland sulfenyl chlorides.
- Startseva,Kuznetsov,Nikitina,Osmanov,Borisov,Matsulevich, Zh. V.,Klochkov
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- Reaction of (+)-carvone with several hetarylsulfenyl chlorides and pyridylselenyl chloride
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New menthane-type derivatives were prepared via hetarylsulfenyl- chlorination reactions of (+)-carvone with 2-benzothiazolyl-, 4,6-dimethyl-2-pyrimidyl-, and 3-methoxycarbonyl-2-pyridylsulfenyl chlorides and 2-pyridylselenyl chloride.
- Kuznetsov,Startseva,Nikitina,Osmanov,Borisov,Matsulevich, Zh. V.,Klochkov
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- Synthesis of Enhanced, Isolable Disulfanium Salts and their Application to Thiiranium-Promoted Polyene Cyclizations
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Although electrophile-promoted polyene cyclizations have long been a mainstay transformation for the rapid and stereocontrolled preparation of varied natural products and designed molecules, efforts to effect sulfur-promoted variants have arguably lagged behind other counterparts. This state of affairs is particularly true with alkyl sulfide-based electrophiles, even in racemic variants. Herein, building on previously reported discoveries, is described a distinct and modular method to prepare a range of isolable alkyl and aryl disulfanium salts that can affect thiiranium-based polyene cyclizations in moderate to good yields. In most of the substrates probed, these reagents provide superior yields to previously reported alternatives. In addition, initial efforts to develop an asymmetric variant of the process through the use of chiral versions of these reagents are discussed.
- Cole, Charles J. F.,Chi, Hyung Min,Debacker, Kenneth C.,Snyder, Scott A.
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p. 4351 - 4358
(2018/06/26)
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- Diaryl and heteroaryl sulfides: Synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents
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A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
- Yonova, Ivelina M.,Osborne, Charlotte A.,Morrissette, Naomi S.,Jarvo, Elizabeth R.
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p. 1947 - 1953
(2014/04/03)
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- Synthesis of aryl thioethers through the N -chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents
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A convenient one-pot approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were then directly reacted with Grignard reagents to provide aryl sulfides in good to excellent yields under mild reaction conditions. Functional groups including ester, fluoro, and chloro are tolerated by the reaction conditions employed. It is important to note that this method has a short reaction time (30 min in total) and represents an alternative approach for the synthesis of aryl sulfides over the existing protocols.
- Cheng, Jun-Hao,Ramesh, Chintakunta,Kao, Hsin-Lun,Wang, Yu-Jen,Chan, Chien-Ching,Lee, Chin-Fa
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p. 10369 - 10374
(2013/01/15)
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- Heterocycle-substituted stable thioaminyl radicals: Isolation, ESR spectra, and magnetic properties
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N-[(2-Benzothiazolyl)thio]- (1), N-[(2-benzoxazolyl)thio]- (2), and N-(2-pyrimidylthio)-2,4,6-trisubstituted-phenylaminyls (3) were generated by oxidation of the corresponding amines. Although 2 and were not sufficiently persistent to be isolated, I was very persistent and could be isolated as radical crystals. The ESR spectra of nondeuterated and partially deuterated 1-3 radicals were measured, and the spin density distributions were estimated from the hyperfine coupling constants. Ab initio molecular orbital calculations were made for 1 to discuss the spin density distribution in more detail. Single-crystal X-ray crystallographic analysis was performed for one radical. Magnetic properties were measured for isolated four radicals with a SQUID. Two radicals showed ferromagnetic interaction, and analyses of (x)T vs T plots with the one-dimensional regular Heisenberg model gave 2J/k(B) =5.8 and8.6K. The remaining two radicals showed antiferromagnetic interaction. Analyses of the (x)T vs T plots with the Curie-Weiss law or dimer model gave Θ = -1.4 K and 2J/k(B) = -1370K. The strong antiferromagnetic interaction could be explained in terms of the X-ray crystallographic results.
- Miura,Tomimura,Teki
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p. 7889 - 7895
(2007/10/03)
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- Cyclization of N-butyl-4-pentenylaminyl: Implications for the cyclization of alkenylaminyl radicals
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The utility of arenesulfenamides as aminyl radical precursors has been clearly demonstrated. The cyclization of N-butyl-4-pentenylaminyl is shown to be a slow and irreversible process that is accelerated significantly by small amounts of bis(tributyltin) oxide.
- Maxwell, Brendan J.,Tsanaktsidis, John
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p. 4276 - 4283
(2007/10/03)
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- Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones
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The conditions for the title reaction were studied for the 2-benzothiazole and 2-pyridine series and for some examples in the 2-pyrimidine series.The olefin preparations were generally observed to be more efficient for 2-BT-sulfone systems.From the data of the hundred cases studied, it can be concluded that (E)-olefins are obtained: (i) from saturated BT-sulfones and aromatic aldehydes; and (ii) from benzylic BT-sulfones and branched saturated aldehydes (isobutyraldehyde, pivalaldehyde) or α,β-ethylenic or aromatic aldehydes. (Z)-olefins arise: (i) fom propargylic BT-sulfones and saturated or aromatic aldehydes; and (ii) from allylic or benzylic Pyr-sulfones and saturated aldehydes.Possible mechanisms for this new olefination procedure were examined. - heteroaromatic sulfones, organolithium derivatives, intramolecular ipso reactions, stereochemistry, elimination, olefination.
- Baudin, J. B.,Hareau, G.,Julia, S. A.,Lorne, R.,Ruel, O.
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p. 856 - 878
(2007/10/02)
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- 1-(2-Benzothiazolylthio)-piperidines
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A 1-(2-benzothiazolylthio)-piperidine compound of the formula: STR1 WHEREIN R is a lower alkyl group substituted at least at the 3, 4 and/or 5 positions and n is an integer from 1 to 3, which is prepared by the reaction of 2-mercaptobenzothiazole or its reactive derivative with an alkylated piperidine or its N-halogenated derivative and useful as a vulcanization accelerator having an improved scorching property.
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