87413-32-9

Upstream product

• 2562-37-0 1-nitrocyclohexene 
• 873-55-2 sodium benzenesulfonate 
• 25932-11-0 benzenesulfinic acid sodium dihydrate 
• 134427-69-3 cyclohex-2-enyl phenyl sulfide 
• 690232-46-3 4-methyl-benzenesulfinic acid 2-cyclohexen-1-yl ester 
• 1165952-91-9 cyclohexa-1,3-diene 
• 618-41-7 Benzenesulfinic acid 
• 1521-51-3 rac-3-bromocyclohexene 
• 133957-59-2 2-(trimethylsilyl)ethyl benzenesulfenate 
• 59059-70-0 1-(phenylsulfonyl)cyclohexene 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 58329-99-0 cyclohex-2-enyl methyl carbonate 
• 76644-52-5 rac-3-acetoxycyclohexene 

Downstream Products

• 930-68-7 cyclohexenone 
• 65825-69-6 (1R,2R,6R)-2-Benzenesulfonyl-7-oxa-bicyclo[4.1.0]heptane 
• 65825-69-6 (1S,2R,6S)-2-Benzenesulfonyl-7-oxa-bicyclo[4.1.0]heptane 
• 1165952-92-0 cyclohexa-1,4-diene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 618-41-7 Benzenesulfinic acid 
• 193824-92-9 2-(1-Benzenesulfonyl-cyclohex-2-enyl)-ethanol 
• 882426-33-7 2-(cyclohexa-1,3-dien-1-yl)ethyl methanesulfonate 
• 882426-34-8 (2-Cyclohexa-1,3-dienyl-ethyl)-((S)-1-phenyl-ethyl)-amine 
• 882426-35-9 Ethenesulfonic acid (2-cyclohexa-1,3-dienyl-ethyl)-((S)-1-phenyl-ethyl)-amide 
• 882426-37-1 (1R,6S,8S)-4-((S)-1-Phenyl-ethyl)-5-thia-4-aza-tricyclo[6.2.2.0^1,6]dodec-9-ene 5,5-dioxide 
• 882426-36-0 (1S,6R,8R)-4-((S)-1-Phenyl-ethyl)-5-thia-4-aza-tricyclo[6.2.2.0^1,6]dodec-9-ene 5,5-dioxide 
• 71647-38-6 1-(2-hydroxyethyl)-1,3-cyclohexadiene 
• 193824-94-1 2-(2-Cyclohexa-1,3-dienyl-ethoxy)-tetrahydro-pyran 

Relevant academic research and scientific papers

Base-Mediated Radical Borylation of Alkyl Sulfones

A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal-free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B2neop2), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late-stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.

Nature of the intermediates in gold(I)-catalyzed cyclizations of 1,5-enynes

The carbene or carbocationic nature of the intermediates in the gold-catalyzed cycloisomerization of 1,5-enynes can be revealed, depending on the ligands on the gold catalysts. Gold complexes with highly electron-donating ligands promote reactions that proceed via intermediates with carbene-like character, leading to products with a bicyclo[3.1.0]hexene skeleton. The intermediate cyclopropyl endo-gold carbenes formed in this cyclization have been trapped, for the first time, to give biscyclopropane derivatives in a reaction that proceeds in a concerted fashion, according to DFT calculations.

An expeditious entry to benzylic and allylic sulfones through byproduct-catalyzed reaction of alcohols with sulfinyl chlorides

(Chemical Equation Presented) In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellen

Catalyst-free alkylation of sulfinic acids with sulfonamides via sp 3 C-N bond cleavage at room temperature

An unprecedented catalyst-free alkylation of sulfinic acids with sulfonamides has been developed via sp3 C-N bond cleavage at room temperature. In the absence of external catalysts and additives, a wide variety of N-benzylic and N-allylic sulfonamides couple with sulfinic acids to give structurally diversified sulfones in moderate to excellent yields. Furthermore, the reaction of N-(2-acyl)allylic sulfonamides with sulfinic acids provides a convenient access to trisubstituted allyl sulfones with exclusive Z selectivity.

ARYL CARBOXYLIC ACID CYCLOHEXYL AMIDE DERIVATIVES

A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof: (I) wherein the variants R and X are defined in the specification.

π-Allylic sulfonylation in water with amphiphilic resin-supported palladium-phosphine complexes

π-Allylic substitution of allyl esters with sodium arylsul-finate was performed with an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-supported phosphine-palladium complex in water as a single reaction medium under heterogeneous conditions to give allyl sulfones in good to high yields. Catalytic asymmetric allylic substitution of cycloalkenyl esters also took place in water using a PS-PEG resin-supported chiral imidazo-indolephosphine- palladium complex to give cycloalkenyl sulfones with up to 81% ee.

Ionic liquid/water as a recyclable medium for Tsuji-Trost reaction assisted by microwave

An efficient microwave protocol is described for allylic substitution with various carbon and heteronucleophiles catalyzed by Pd(OAc)2/TPPTS in an [EMIm]BF4/H2O medium. The ionic liquid/water containing catalyst system can be recycled eight times without loss of activity.

Towards asymmetric catalysis in the major groove of 1,1′-binaphthalenes

Four new diphosphane ligands, (R)-4, (R)-5, (S)-6, and (R)-7 (Schemes 3, 4, 6, and 7), featuring metal-coordination sites located in the major groove of chiral 1,1′-binaphthalene clefts, were prepared in enantiomerically pure form. The performance of this new class of ligands was tested in enantioselective, Pd-catalyzed allylic alkylation reactions with acyclic and cyclic methyl carbonates 28-30 as substrates under various reaction conditions (Schemes 8 and 9). Using sodium phenyl sulfinate as a nucleophile, the reactivity of the catalysts formed with the new ligands and suitable palladium precursors was found satisfactory (> 90%); however, the ee values were in all cases poor (31P-NMR-Spectroscopic investigations revealed the formation of multiple-catalyst species in solution (Fig. 2), and molecular modeling suggested a lack of embedding of the coordinated substrate in a 'chiral pocket' (Fig. 3), which probably accounts for the observed low level of enantioselectivity.

Cathodic behaviour of 1-cycloalken-1-yl phenyl sulfones. I. Competition among dimerization, cleavage, isomerization and oligomerization processes in aprotic media

1-Cycloalken-1-yl phenyl sulfones 1a and 1b have been studied electrochemically in aprotic media (N,N-dimethylformamide, dimethyl sulfoxide, or acetonitrile containing tetraalkylammonium salts) at a mercury electrode. Their behaviour has been compared with that of 2-norbornen-2-yl phenyl sulfone 1c. The expected cleavage reaction is accompanied by a concomitant isomerization process into allyl sulfones that is triggered by electrogenerated bases. A quantitative determination of the product distribution during controlled-potential electrolyses suggests the formation of dimers and oligomeric species, arising through a Michael addition of the sulfone anions to the activated double bond of these sulfones.

Phenylsulfonyl as a β participating group

The phenylsulfonyl group (PhSQ2) has been examined for its β effect properties. The stereochemical relationship was varied between phenylsulfonyl and a nucleophilic leaving group (nucleofuge) separated by two carbons. Mechanisms were distinguished through solvent effects on rates and products. When the stereochemistry between the two groups was gauche, the only effect of phenylsulfonyl was strong inductive retardation in a mechanism involving solvent participation. With the antiperiplanar stereochemistry, however, the mechanism clearly changed to carbocation formation with a small kinetic acceleration. Thus, phenylsulfonyl is a weak β effect substituent. This remarkable property for a strongly electron-withdrawing group occurs most likely through hyperconjugation or possibly through anchimeric assistance.