The stereochemistry of the cathodic pinacolization of carbonyl compounds: The configuration of benzoin pinacol

Juday, Richard E.; Waters, William L.

doi:10.1016/s0040-4039(00)91113-4

Cited by 3 publications

(5 citation statements)

References 9 publications

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“…Waters et al have reported that 4,5,6,7-tetraphenyl-1,3-dioxathiepan 2-oxide undergoes desulfoxylation to afford a tetrahydrofuran derivative by simply heating above the melting point (Scheme 4). 5 Substituents on the 4-and 7-positions of the seven-membered cyclic sulfites seem to be unfavorable to polymerization.…”

Section: Resultsmentioning

confidence: 99%

“…5 Substituents on the 4-and 7-positions of the seven-membered cyclic sulfites seem to be unfavorable to polymerization.…”

Section: Methodsmentioning

confidence: 99%

“…Mp: 66-67°C (lit. 5 Synthesis of 4-Phenyl-1,3-dioxa-2-thiepane 2-Oxide (7PhCS). A solution of thionyl chloride (15.0 g, 126 mmol) in chloroform (370 mL) was added dropwise at 0°C into a solution of 1-phenyl-1, 4-butanediol (18.4 g, 111 mmol) and pyridine (20.0 g, 253 mmol) in chloroform (740 mL).…”

Section: Methodsmentioning

confidence: 99%

“…The solid was recrystallized from diethyl ether to give 1-phenyl-1,4-butanediol in 88% yield. Mp: 66−67 °C (lit . mp 65−66 °C).…”

Section: Methodsmentioning

confidence: 99%

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Cationic Polymerization of Seven-Membered Cyclic Sulfites. Substituent Effect on the Polymerization Behavior

et al. 1998

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The syntheses and cationic polymerizations of seven-membered cyclic sulfites having phenyl (7PhCS), benzo (7BnCS), and cyclohexane (7CyCS) groups were examined. 7PhCS and 7CyCS underwent complete elimination of SO 2 to afford the corresponding tetrahydrofuran derivatives under the cationic conditions. On the other hand, 7BnCS underwent cationic polymerization in the presence of cationic initiators such as TfOH, TfOMe, SnCl4, TsOMe, and MeI in bulk or chlorobenzene to afford the corresponding polymer with M h n 950-8700 without desulfoxylation. The benzo group was operative for polymerization and suppression of desulfoxylation. The polymerization of 7BnCS did not show equilibrium character. The steric hindrance of the benzene ring might be effective to suppress a back-biting reaction. The volume expansion during the polymerization of 7BnCS was 8.57%. This might be caused by the larger dipole-dipole interactions between the monomers and smaller ones between the polymers.

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Section: Resultsmentioning

confidence: 99%

“…5 Substituents on the 4-and 7-positions of the seven-membered cyclic sulfites seem to be unfavorable to polymerization.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…The solid was recrystallized from diethyl ether to give 1-phenyl-1,4-butanediol in 88% yield. Mp: 66−67 °C (lit . mp 65−66 °C).…”

Section: Methodsmentioning

confidence: 99%

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Cationic Polymerization of Seven-Membered Cyclic Sulfites. Substituent Effect on the Polymerization Behavior

et al. 1998

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“…W^prod = 2 log [1 -/ex]/log [1 -</r +/d)] (11) In an attempt to capture the reaction intermediate, phenacyl chloride was electrolyzed in anhydrous DMF containing 1-5% v/v acetic anhydride. The product mixture recovered after electrolyzing for 30 min at -2.2 V contained 21% acetophenone, 56% acetophenone enol acetate, plus ca.…”

Section: Phcoch2clmentioning

confidence: 99%