Reaction of α-methylstyrene with arylsulfonyl chlorides: spontaneous dehydrochlorination against the Zaitsev rule

Ermolaeva, V. V.; Герасимова, Н. П.; Nozhnin, N. A.; Moskvichev, Yuri A.; Alov, E. M.; Danilova, A. S.; Shutova, I. V.; Козлова, О. С.

doi:10.1070/mc2005v015n02abeh001930

Cited by 4 publications

(2 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[11][12][13] Alternatively, the stoichiometric oxidation 14 of sulfides with strong oxidants has also provided allylsulfones. 1 Other alternatives from alkenes include metal catalyzed (e.g., Pd 7,15,16 & Cu 17 ) and substitutions [18][19][20] reactions. Couplings of allylic alcohols with sulfinyl chlorides, 21 activated by NBS, 22 or catalyzed by Pd 3,23 have afforded allylsulfone.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement

Blé-González,

Isbel,

Ojo

et al. 2023

New J. Chem.

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

“…1 Other alternatives from alkenes include metal catalyzed ( e.g. , Pd 7,15,16 & Cu 17 ) and substitutions 18–20 reactions. Couplings of allylic alcohols with sulfinyl chlorides, 21 activated by NBS, 22 or catalyzed by Pd 3,23 have afforded allylsulfone.…”

Section: Introductionmentioning

confidence: 99%

Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement

Blé-González,

Isbel,

Ojo

et al. 2023

New J. Chem.

View full text Add to dashboard Cite

show abstract

Reaction of α‐Methylstyrene with Arylsulfonyl Chlorides: Spontaneous Dehydrochlorination Against the Zaitsev Rule.

et al. 2005

View full text Add to dashboard Cite

Sulfones Q 0600Reaction of α-Methylstyrene with Arylsulfonyl Chlorides: Spontaneous Dehydrochlorination Against the Zaitsev Rule. -The CuCl2-mediated free-radical addition of arylsulfonyl chlorides (I) to α-methylstyrene is accompanied by spontaneous dehydrochlorination of the initial adducts [→(III)]. -(ERMOLAEVA, V. V.; GERASIMOVA, N. P.; NOZHNIN*, N. A.; MOSKVICHEV, Y. A.; ALOV, E. M.; DANILOVA, A. S.; SHUTOVA, I. V.; KOZLOVA, O. S.; Mendeleev Commun. 2005, 2, 84-86; Dep. Chem. Technol., Yaroslavl' State Tech. Univ., Yaroslavl' 150023, Russia; Eng.) -F. Santoso 35-102

show abstract

Allylic C–S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation

et al. 2018

View full text Add to dashboard Cite

A metal-free, open-flask protocol was developed for the preparation of allylic sulfones through direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes. The key step of this process was the Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds. Through this process, the readily available conjugated nitroalkenes can be easily converted into allylic nitro compounds, which contain more reactive C═C bonds toward the sulfonyl radical addition. As a result, allylic sulfones were prepared in excellent yields with a broad substrate scope under mild conditions.

show abstract

Reaction of α-methylstyrene with arylsulfonyl chlorides: spontaneous dehydrochlorination against the Zaitsev rule

Cited by 4 publications

References 11 publications

Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement

Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement

Reaction of α‐Methylstyrene with Arylsulfonyl Chlorides: Spontaneous Dehydrochlorination Against the Zaitsev Rule.

Allylic C–S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation

Contact Info

Product

Resources

About