Corrigendum to “Hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide: selective synthesis of (Z)-1-alkenyl sulfides and selenides” [Tetrahedron 64(47) (2008) 10670–10675]

A Recyclable Biphasic System for Stereoselective and Easily Handled Hydrochalcogenations

“…Physical and spectroscopic data of the following products are identical to those previously reported: (E)-9a, [21] (Z)-9a, [22] (Z)-8a, [22] (E)-8a, [23] (Z)-9b, [22] (E)-9b, [21] (E)-8b, [24] (Z)-8b, [24] (E)-9c, [25] (Z)-9c, [25] (E)-8c, [23] (Z)-8d, [26] (E)-8d, [26] (E)-9e, [27] (Z)-9e, [27] (E)-8e, [28] (Z)-8e, [28] (E)-9f, [29] (Z)-9f, [29] (E)-8f, [30] (Z)-8f. 10 %, 2 mL) and zinc shavings (5 equiv.)…”

“…Major Isomer (Z)-8a: [22,23] 128.8, 128.4, 128.3, 127.7, 126.8, 121.9, 34.2, 34.1, 24.3, 23.9 ppm. Minor Isomer (E)-8a: [24] Identified and measured on the basis of some characteristic 1 H NMR signals that did not present overlaps with those of the major isomer: δ = 7.04 (d, 3 J H,H = 15.7 Hz, 1 H, CH=) and δ = 3.83 (s, 3 H, OCH 3 ) ppm.…”

“…Minor Isomer (E)-9b: [21,22] [25] Isolated by flashchromatography (silica gel, petroleum ether) as Z/E mixture (72: 28 Ethyl 3-(Phenylthio)acrylate (9e): [27] Isolated by flash-chromatography (silica gel, petroleum ether/diethyl ether, 9:1) as Z/E mixture (48:52:), yield 0.062 g (30 %); light-yellow oil. Methyl 3-Phenyl-2-(phenylthio)acrylate (9f): [29] Isolated by flashchromatography (silica gel, petroleum ether/diethyl ether, 9:1) as Z/ E mixture (69:31:), yield 0.116 g (43 %); light-yellow oil.…”

Metal Catalysis in Thiolation and Selenation Reactions of Alkynes Leading to Chalcogen-Substituted Alkenes and Dienes

“…Combination of CuI with rongalite and Cs 2 CO 3 led to Z ‐vinyl chalcogenides as major products starting from dichalcogenides and alkynes (Scheme ) . The catalytic system tolerated a wide range of functional groups well, including methoxy, amino, nitro, amide, hydroxyl, and halogene, both in the alkyne and dichalcogenide moieties.…”