80227-71-0

Upstream product

• 27098-65-3 3-phenylsulfanyl-propionaldehyde 
• 15286-68-7 3-(phenylthio)prop-2-en-1-ol 
• 108-98-5 thiophenol 
• 107-02-8 acrolein 
• 624-67-9 Propargylic aldehyde 
• 90322-80-8 3-(Phenylthio)propenenitrile 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 123776-20-5 (E)-6-Phenylsulfanyl-hex-5-ene-1,4-diol 
• 127459-18-1 5-tert-Butyl-3-phenylsulfanyl-[2,2']bifuranyl 
• 123075-33-2 (E,4SR,5SR)-5-Hydroxy-7-(phenylthio)-2,2,4-trimethyl-6-hepten-3-one 
• 105259-46-9 6-methyl-2-thiophenyl-1,4-naphthoquinone 
• 127459-16-9 5-Methyl-2-phenyl-3-phenylsulfanyl-furan 
• 57341-12-5 2-phenylsulfanyl-[1,4]naphthoquinone 
• 105259-54-9 7-Phenylsulfanyl-naphtho[1,2-d][1,3]dioxole-6,9-dione 
• 127459-09-0 2,5-Bis-(2-methoxy-5-methyl-phenyl)-3-phenylsulfanyl-furan 
• 105245-47-4 5-methoxy-3-phenylsulfanyl-1,4-naphthoquinone 
• 105259-51-6 5,7-Dimethoxy-2-phenylsulfanyl-[1,4]naphthoquinone 
• 105259-55-0 3-Phenylsulfanyl-phenanthrene-1,4-dione 
• 103959-47-3 (E)-(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-5-phenylsulfanyl-pent-4-enethioic acid S-tert-butyl ester 
• 123075-34-3 (E,4SR,5SR)-2,4-Dimethyl-5-hydroxy-7-(phenylthio)-2-((trimethylsilyl)oxy)-6-hepten-3-one 
• 105259-53-8 5,6-Dimethoxy-2-phenylsulfanyl-[1,4]naphthoquinone 

Relevant academic research and scientific papers

A new synthesis of 1-phenylthio- and 1-alkylamino-4-nitrobuta-1,3-dienes

A new synthesis of push-pull dienes such as 4-nitro-1-phenylthiopenta-1,3-diene 4 and 1-dialkylamino-4-nitropenta-1,3-diene 5, is described. The X-ray crystal analysis shows that 4-nitro-1-(pynolidin-1-yl)penta-1,3-diene 5a is essentially planar in an E,E

The origins of the benzotriazole project, its versatility illustrated by a new --C = CHCH+OEt synthon, and novel syntheses of α,β-unsaturated aldehydes and ketones, furans, pyrroles and allyl ethers

A historical introduction describes the discovery and progress of benzotriazole synthetic methodology. 3-(Benzotriazol-1-yl)-1-ethoxyprop-1-ene (6), readily prepared from 3-(benzotriazol-1-yl)-3-ethoxyprop-1-ene (4) via zinc bromide promoted allylic rearrangement, undergoes lithiation and regiospecific single or double 3-alkylation to give products which undergo (i) hydrolysis to afford α,β-unsaturated aldehydes, (ii) silica gel promoted reverse allylic rearrangement of the benzotriazolyl group, followed by further alkylation and subsequent hydrolysis to furnish α,β-unsaturated ketones, (iii) intramolecular cyclizations to construct pyrroles and furans, and (iv) intermolecular nucleophilic substitution with Grignard reagents to provide allyl ethers.

Use of Hine's D Values To Predict the Position of the Equilibrium in the Cope Rearrangement of Multiply Substituted 1,5-Dienes

A series of 1,5-dienes (1a-f) were employed to test whether Hine's D values can predict the position of equilibrium in Cope rearrangements.In the cases of the substituent pairs , ,, , and , equilibrium constants calculated with Hine's D values gave reasonable agreement with those obtained experimentally.Dienes 1g-i were prepared to test whether reduction of the ?-donating character of a nitrogen substituent (carbamoyl vs dimethylamino) would change the directing ability of the nitrogen group.The aggregate order of directing ability was N(CH3)2 > OCH3 > EtO2CN(CH3) > CH3 > H>.Diene 15a, with a more complicated substitution pattern (OCH3 and CH3 versus CH3 and H) not directly amenable to analysis with D values, can be considered to reduce to the case of .The experimental Keq obtained agreed with that expected for the pair.Dienes 15c and 16b, designed to test the pairs and , respectively, decomposed under the gas phase conditions of the rearrangement.Attempts to effect rearrangement with Pd(II) catalysis failed.

Acyl Radical Cyclizations in Synthesis. Part 3. Synthesis of (+/-)-trans-3,5-Bis(t-butyldimethylsiloxy)-2-Methylenecyclohexanone, an 'A' Ring Model for 1α,25-Dihydroxyvitamin D3

A concise synthesis of (+/-)-trans-3,5-bis(t-butyldimethylsiloxy)-2-methylenecyclohexanone has been developed.The synthesis proceeds in seven steps from ethyl acetoacetate and involves a highly efficient acyl radical cyclization to construct the six-membered ring.

Reversal of Stereochemistry in the Aldol Reactions of a Chiral Boron Enolate

A novel route to optically active anti aldols of certain aldehydes is presented.The boron enolate derived from oxazolidinone 3 reacts with various aldehydes to give either syn or anti aldols, depending on the amount of dibutylboron triflate used in the en

A NOVEL NAPHTOQUINONE SYNTHESIS VIA TANDEM DIRECTED LITHIATIONS

A convenient one-pot synthesis of 1,4-naphtoquinones from tertiary benzamides has been devised using tandem directed lithiations.

Oxidation of Alcohols with tert-Butyl Hydroperoxide and Diaryl Diselenide

Treatment of alcohols with tert-butyl hydroperoxide in the presence of diaryl diselenide in refluxing benzene gives the corresponding aldehydes or ketones.Although some allylic alcohols undergo oxidation in the presence of 10-15 mol percent of bis(p-chlorophenyl) diselenide, use of 0.5 equiv of bis(2,4,6-trimethylphenyl) diselenide gives satisfactory results in almost all cases.The procedure can be used for selective oxidation of alcohols bearing a phenylthio or phenylseleno group, which usually survives the reaction conditions to give the corresponding carbonyl compounds.