24463-89-6

Upstream product

• 70398-35-5 (tetrahydrothiophen-2-yl)triphenylphosphonium chloride 
• 100-52-7 benzaldehyde 
• 14267-92-6 1-chloro-4-pentyne 
• 591-50-4 iodobenzene 
• 24463-87-4 (5-chloropent-1-ynyl)benzene 
• 21777-85-5 cyclopropylphenylethyne 
• 140696-74-8 2-benzyl-2-(methylthio)thiolane 
• 77213-97-9 5-Mercapto-1-phenyl-pent-1-in. 

Downstream Products

• 24463-88-5 (Z)-2-benzylidenetetrahydrothiophene 2-oxide 

Relevant academic research and scientific papers

Synthesis of cyclic sulfides by nickel complexes catalyzed electroreduction of unsaturated thioacetates and thiosulfonates

Functionalized cyclic sulfides with four to six membered rings were synthesized by ring closure of the labile thiols which were formed in situ by the nickel complex catalyzed electroreduction of the thioacetates and thiosulfonates having suitably placed e

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

(: Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K

This protocol provides a novel, environmentally friendly and simple method for the synthesis of (Z)-tetrahydrothiophene derivatives using the nucleophilic thiyl radical intramolecular cycloaddition cascade process to construct C-S bonds under transition-m

Trisulfur Radical Anion (S3?-) Involved [1 + 2 + 2] and [1 + 3 + 1] Cycloaddition with Aromatic Alkynes: Synthesis of Tetraphenylthiophene and 2-Benzylidenetetrahydrothiophene Derivatives

S3?--mediated [1 + 2 + 2] and [1 + 3 + 1] cycloaddition reactions of aromatic alkynes to give tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives via two C-S bond formations are developed. These two protocols provide new, simple, and straightforward strategies to construct tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives under transition-metal-free conditions. This study also expands the application of S3?- in organic reactions.

C,C-Coupling with sulfur-stabilized carbanions - 6. Preparation and electrophilic substitution of 1-[3-methyl-2-(2-thioanylthio)-butyl]piperidine and dethioacetalization of semicyclic dithioacetals

1-[3-Methyl-2-(2-thioanylthio)butyl]piperidine (8) is obtained from L-valine via enantiomerically pure 1-(2-mercapto-3-methylbutyl)piperidine (6). The diastereoisomers are separated by column chromatography and the reactions of the carbanion 8a with elect

Heterocyclisation radicalaire de thiols acetyleniques

Photolysis of pent-4-yne-1-thiol 1 leads to a mixture of thiacyclohex-2-ene 2, 2-methylenethiacyclopentane 3 and 2-methylthiacyclopent-2-ene 4 with overall yield of up to 60 percent.Compound 2 is always amply predominant and can, according to the experimental conditions, make up to 100 percent of the mixture.Compounds 2 and 3 are assumed to derive from the thiyl radical, which adds essentially to the terminal position of the triple bond.The addition reaction is reversible, with the radical leading to compound 3 (five-membered ring) being kinetically favoured, as shown by temperature and concentration effects on the ratio 2/3.The use of deuteriated thiols shows the hydrogen transfer step to be irreversible and to proceed from the thiol itself.This study has been extended to the substances HCC(CH2)nSH 1a (n = 2 to 6).Again, we obtained essentially or exclusively the compound 2a resulting from preferential addition to the terminal position of the triple bond.The same substrates thus lead regioselectively either to the heterocycles 2a or to the heterocycles 3a, according to whether formation of the thiyl radical or of the thiolate anion is favoured.Therefore these two processes are synthetically complementary.The introduction of a heteroatom Y into the chain does not seem to entail any important modification of the course of the radical cyclization reaction itself.Indeed, the substances HCCCH2Y(CH2)2SH 1b (Y = O, S, NR) again lead essentially to substances 2b.However, a new heterocyclic substance 4b is formed, the origin of which is attributed to the isomerization of the triple bond of the initial substrate 1b, facilitated by the heteroatom Y.An alkyl group in the terminal position of the triple bond, on the other hand, entirely modifies the regioselectivity of the reaction.The substrates RCC(CH2)nSH 1a (R = Me, Ph; n = 2 to 5) lead essentially to product 3a, resulting from addition on the non-terminal position of the triple bond.This trend is particularly clear when R = Ph, a fact attributed to the benzylic character of the intermediate radical : only compounds 3a are then isolated, with excellent yields (86 percent for n = 3, 89 percent for n = 4).Nevertheless, the results of this exploratory study cannot be used in a quantitative manner to establish regioselectivity rules regarding intramolecular addition to an acetylenic system.This remark especially stems from a more elaborate study of the by-products formed by photolysis of pent-4-yne-1-thiol 1.In some cases an isomeric heterocyclic product 4 is formed which can be showed not to result from isomerization of 2 and to result only partially from isomerization of 3.This led us to suggest that it is formed by isomerization of the initial acetylenic thiol 1 to the isomeric allenic thiol.On the other hand, even in the high dilution conditions used, we isolated polymers and dimers with yields of 20 to 60 percent.The dimers, which could be analyzed, are a mixture, often complex but essentially composed of substances 5 (widely predominant) and 6.These products could arise from regioselective add...