75712-22-0Relevant articles and documents
Synthesis of vinyl sulphides, azido sulphides, and olefins from β-hydroxy-sulphides
Dumont, Willy,Krief, Alain
, p. 673 - 675 (1980)
Vinyl sulphides, azido sulphides, and olefins have been prepared from β-hydroxy-sulphides via β-chloro-sulphides; the regio- and stereo-chemistry of these reactions is discussed.
Thiol mediated 5-(π-endo)ortho vinyl radical cyclizations
Montevecchi, Pier Carlo,Navacchia, Maria Luisa
, p. 201 - 219 (2007/10/03)
The radical reaction of benzenethiol with alkynes 1a-o carried out at 154 °C affords a mixture of thiol/alkyne adduct 3 and benzothiophene 5, deriving from vinyl radical intermediates 2 through hydrogen abstraction and 5-(π-endo)(orthocyclization onto the
Application of Free Radical Substitution Reaction into Interconversion of 1-Alkenylsulfides, 1-Alkenylgermanes, and 1-Alkenylstannanes
Ichinose, Yoshifumi,Oshima, Koichiro,Utimoto, Kiitiro
, p. 669 - 672 (2007/10/02)
Treatment of 1-alkenylsulfides or 1-alkenylstannanes with Ph3GeH in the presence of Et3B provides 1-alkenyltriphenylgermanes in good yields. 1-Alkenylstannanes are converted into 1-alkenylsulfides easily with PhSH-Et3B, whereas 1-alkenyltriphenylgermanes are recovered unchanged upon treatment with Ph3SnH-Et3B or PhSH-Et3B.
Et3B Induced Radical Addition of Thiols to Acetylenes
Ichinose, Yoshifumi,Wakamatsu, Kuni,Nozaki, Kyoko,Birbaum, Jean-Luc,Oshima,Koichiro,Utimoto, Kiitiro
, p. 1647 - 1650 (2007/10/02)
Thiols added easily to acetylenic compounds in the presence of Et3B to give alkenyl sulfides in good yields.The reaction of acetylenes with 3-methyl-2-buten-1-thiol gave dihydrothiophene derivatives in one pot.
A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds
Ochiai, Masahito,Ukita, Tatsuzo,Fujita, Eiichi,Tada, Shin-ichi
, p. 1829 - 1839 (2007/10/02)
Organosulfur compounds on treatment with butyllithium in tetrahydrofuran followed by tributylstannylmethyl iodide 1 afforded olefins.The reaction was found to proceed via the destannylsulfurization of the initially formed β-stannyl organosulfur compounds.Thus, allyl 2-pyridyl sulfides 2 or allyl phenyl sulfones 12 were converted into 1,3-dienes 4.Compounds 13 and 15 were converted into the olefins 14 and 17.Furthermore, the reaction was applied to the synthesis of α-substituted vinyl sulfides 24 and allene 27.The stereochemistry of the double bond is discussed.Keywords - destannylsulfurization; allyl 2-pyridyl sulfide; allyl phenyl sulfone; synthesis of olefin; 1,3-diene; vinyl sulfide; β-tributylstannyl organosulfur compound.