Acid-catalyzed hydrolysis of ring-substituted phenyl vinyl sulfides

Regioselective functionalization of bicyclic piperazinedione bridgehead carbanions

“…'H NMR (100 MHz) (CDC13) (Me4Si) 1.57 (3 H, s), 1.81-1.99 (2 H, m), 2.99 (3 H, s), 3.07 (3 H, s), 3.86 (2 H, m), 5.01 (1 H, s); IR (NaCl, neat) 1670, 1390, 1240, 1180, 1045 cm"1; mass spectrum, m/e 198 (M+, 24.9%), 184 (5.2), 141 (41.6), 56 (100).…”

“…3.4-3.73 (3 H, m),5.05 (1 H, s), 5.96 (1 H, d, / = 5.6 Hz),7.3 (5 H, m); IR (NaCl, neat) 3320, 1675, 1660, 1460, 1410, 1330, 1270, 1250, 1115, 1100, 1075, 1060, 745 cm"1; mass spectrum, m/e 198 (100%), 169 (30.8), 141 (18.3), 105 (29.3).Anal. …”

Structure and reactivity of .alpha.,.beta.-unsaturated ethers. 16. Electrophilic addition of benzenesulfenyl chloride to .alpha.,.beta.-unsaturated ethers and sulfides

“…Commercial ethyl (3), n-butyl (6), and isobutyl vinyl ethers (7) were distilled from LÍAIH4. Methyl (2) and tert-butyl vinyl ethers (5) were prepared by the alcohol exchange of 3 and 6, respectively.5 Isopropyl vinyl (4) and other alkenyl alkyl ethers (9)(10)(11)(12)(13)(14)(15) were obtained by the pyrolysis of an appropriate acetal as described previously.6 Preparations of phenyl vinyl ether (8),71,2-dimethoxyethylene (16),8 alkyl vinyl sulfides (17-20),9 and phenyl vinyl sulfide (21)10 were described before. Styrene (22) was distilled from teri-butylcatechol just before use.…”

“…Similar results were found in the hydrations of alkyl ethynyl ethers15 and sulfides16 as well as in the hydrolysis of aryl vinyl ethers and sulfides. 10 The difference in the efficiency of electronic transmission between the O and S atoms may be attributed to their lone pair electrons in 2p and 3p orbitals. Anomalies found in the hydrolysis of alkyl vinyl sulfides {p* > 0)9 were not observed here in the sulfenyl chloride addition.…”