1981
DOI: 10.1021/ja00410a051
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α-Disulfoxide and sulfinic anhydride in the peroxy acid oxidation of 2-methyl-2-propyl 2-methyl-2-propanethiosulfinate

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Cited by 48 publications
(14 citation statements)
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“…Since 3a‐ 18 O‐1 as another main product was observed in our labeling experiment, we propose a plausible pathway. It was deduced that the hydrolysis of disulfoxide 7 ,,, would generate benzenesulfinic acid ( G ) which was converted into an oxygen‐centered radical ( H ) resonating with sulfonyl radical A via the single electron transfer (SET) and deprotonation process in the presence of persulfate . The further reaction between A and 1a would lead to the selective formation of the final product.…”
Section: Resultsmentioning
confidence: 99%
“…Since 3a‐ 18 O‐1 as another main product was observed in our labeling experiment, we propose a plausible pathway. It was deduced that the hydrolysis of disulfoxide 7 ,,, would generate benzenesulfinic acid ( G ) which was converted into an oxygen‐centered radical ( H ) resonating with sulfonyl radical A via the single electron transfer (SET) and deprotonation process in the presence of persulfate . The further reaction between A and 1a would lead to the selective formation of the final product.…”
Section: Resultsmentioning
confidence: 99%
“…Z isomer: NMR (CDC13) 2.00 (m, 9, 2-H, 3-H, 4-H, 7-Me), 2.90 (m, 1, 1-H), 4.05 (q, 7 = 9 Hz, 5-H), 6.00 (d, 7 = 7 Hz, 8-H), 10.20 (d, 7 = 7 Hz, CHO); IR (CHC13) 2860, 2810, 1720, 1660 cm"1; CI-MS 199 ( + 1)+. £ isomer: NMR (CDC13) 2.00 (m, 6, 2-H, 3-H, 4-H), 2.20 (s, 3, 7-Me), 6 (d, 7 = 7 Hz, 8-H), 10.2 (d, 7 = 7 Hz, CHO); IR (CDC13) 2860, 2810, 1720, 1660 cm"1; CI-MS 199 ( + 1)+.…”
Section: Methodsmentioning
confidence: 99%
“…The crude oil was chromatographed and eluted with a mixture of hexane/ether, 1/1, to give 40 mg of a mixture of cis and trans nitriles. UV (EtOH) Xma, 315 nm (< 24000); NMR (CDC13) 1.7 (m, 6, 2-H, 3-H, 4-H), 1.85 (s, 3, 7-Me), 2.05 and 2.20 (s, 3, 11-Me, mixture of cis and trans), 2.7 (m, 2, 1-H, 5-H), 6.1 (m, 3, 8-H, 10-H, 12-H), 6.9 (m, 1, 9-H); IR (CHC13) 2840,2200,1710,1590 cm"1; CI-MS 246 ( + 1)+.…”
Section: Condensation Of 19b With Pyrrolidine Perchlorate and L(-)-pr...mentioning
confidence: 99%
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“…[6][7][8] Oxidation of aromatic disulfides with Pb(OAc) 4 in alcohols resulting in sulfinic esters is most extensively studied. 9 Chlorine dioxide was success fully used in the synthesis of dialkyl and diaryl thiosul fonates, sulfonic acids, and sulfonyl chlorides.…”
Section: Resultsmentioning
confidence: 99%