Reaction of arylsulfonyl compounds with excess organolithium reagents. Communication 16. Selectivity in the metallation of phenyl thienyl sulfones. relative reactivity of the benzene and thiophene rings
The relative acidity of the aromatic hydrogen atoms in sulfonyl-substituted benzene and thiophene derivatives has not been determined. Therefore, the authors obtain important information on this subject by studying the metallation of phenyl thienyl sulfones. Depending on the nature of the solvent employed, phenyl 2-thienyl sulfone undergoes metallation with 1 equiv. of BuLi either in position 3 or 5 of the thiphene ring; treatment with 4 equiv. of buLi results in the predominant formation of 2,3',5'-trilithio derivative. Metallation of phenyl 3-thienylsulfone with 1 equiv. of BuLi occurs in position 2 of the ring, whereas reaction with 4 equiv. of BuLi gives primarily the 2,2',4'-trilithio derivative. Competitive metallation reactions demonstrated that all thiophene sulfones are more easily metallated than benzene sulfones.
- Research Organization:
- N.D. Zelinskii Institute of Organic Chemistry, Acad. of Sci., Moscow
- OSTI ID:
- 7059797
- Journal Information:
- Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 34:4, PT. 2; ISSN BACCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
ALKALI METAL COMPOUNDS
AROMATICS
ARYL RADICALS
BENZENE
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
ENERGY
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
KINETICS
LITHIUM COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
ORGANOMETALLIC COMPOUNDS
RADICALS
REACTION KINETICS
SULFONES
THIOPHENE
THIOPHENOLS