Sulfides alkynyl alkyl

Sulfides are readily formed from thiols on reaction with halides (including glyco-syl halides) or epoxides in the presence of a phase-transfer catalyst. In aqueous micelles of cetyltrimethylammonium bromide the reaction of Na2S with haloalkanes generates symmetrical sulfides. Alkynyl phenyliodonium salts are suitable electrophiles for S-alkylation of O.O -dialkyl phosphorodithiolates. ... 

SYNTHESIS OF THIOETHERS, SULFONES, AND RELATED COMPOUNDS Example 5.5 Preparation of an Alkynyl Alkyl Sulfide [103],... 

Nucleophilic reactions of lithium thioalkynolates with electrophiles mostly occur at the 3 -position to afford alkynyl sulfides. For example, 3 -silylation and 3 -stannation are shown in equation 80 the synthesis and -alkylation of a quaternary ammonium thioalkynolate are shown in equation 81. Exceptionally, lithium thioalkynolates add to ketones to form -thiolactones, which are converted into alkenes on elimination of carbon oxysulfide (equation 82). Contrary to lithium ynolates, thioalkynolates do not react with aldehydes. ... 

Metallation of various 1-alkynyl sulfides, followed by alkylation of the resulting anion leads exclusively to a-alkylated allenyl sulfides (Scheme 39). 

Sasaki M, Tanino K, Miyashita M (2001) Stereospecific alkyl and alkynyl substitutimi reactions of epoxy sulfides with organoaluminums with double inversion of the configuration. J Org Chem 66 5388-5394... 

Olefinic aldehydes have been synthesized by a variety of methods including oxidation of the corresponding primary alcohols with the chromium trioxide-pyridine complex 195—197) or N-chlorosuccinimide-dimethyl sulfide complex 198), heating a primary alken-l-yl mesylate with dimethylsulfoxide 199), or by alkylation of the lithium salt of 5,6-dihydro-2,4,4,6-tetramethyl-l,3-(4H)-oxazine with an alkynyl iodide followed by sodium borohydride reduction and acid hydrolysis (200). 

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