A novel palladium(0)-catalyzed addition of diphenyl disulfide to allenes leading to vicinal disulfides and its application to carbonylation with carbon monoxide

Tetrahedron Letters

Volumn 48, Issue 36, 2007, Pages 6312-6317

  Kodama, Shintaro ^a   Nishinaka, Etsuyo ^a   Nomoto, Akihiro ^a   Sonoda, Motohiro ^a   Ogawa, Akiya ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Allenes; Bisthiolation; Carbon monoxide; Diphenyl disulfide; Tetrakis(triphenylphosphine)palladium(0)

Indexed keywords

ALLENE DERIVATIVE; CARBON MONOXIDE; DIPHENYL DISULFIDE; PALLADIUM; SULFIDE; TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM; UNCLASSIFIED DRUG; VICINAL DISULFIDE;

ADDITION REACTION; ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COVALENT BOND; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 34547684127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.019     Document Type: Article

References (28)

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23. 2 to 1a in the presence of galvinoxyl to the reaction mixture. As a result, the bisthiolation of 1a proceeded successfully.
24. 1H NMR spectroscopy. The purification of the products was performed by preparative TLC on silica gel using hexane/AcOEt = 100:0-96:4 as an eluent.
25. 2: C, 74.06; H, 7.10; S, 18.83. Found: C, 73.78; H, 6.97; S, 18.54.
26. 1H NMR spectra: the E/Z ratio of 2a (time) = 96/4 (4 h); 94/6 (10 h); 93/7 (20 h). However, the purification using preparative TLC on silica gel resulted in the formation of Z-isomer of 2a (E/Z = 67/33).
27. 2 to 1c was conducted with heating at 75 °C, resulting in the formation of the regioisomer 11c of 2c, that is, the bisthiolation product at the inner carbon-carbon double bond of 1c in 9% yield.{A figure is presented}
28. The E/Z ratios of 9c and 10c were tentatively determined by the comparison of the E/Z ratios of the selenative carbonylation products (6 and 8).