Ortho metalation of N-substituted benzenesulfonamides by excess N-butyllithium. Condensation with carbonyl compounds. Cyclizations

H Watanabe, RL Gay, CR Hauser

Index: Watanabe,H. et al. Journal of Organic Chemistry, 1968 , vol. 33, # 2 p. 900 - 903

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Citation Number: 46

Abstract

(1) Supported by the Army Reaearch Office (Durham) and by Public Health Service Reaearch Grant No. CA 04465-09 from the National Cancer Inatitute. benzenesulfonamides (1) undergo ortho metalation, as well as N-metalation, with excess n-butyllithium to form dilithiosulfonamides 2, as evidenced by condensations with carbonyl compounds to give ortho derivatives (Scheme I, Table I). ortho Metalation was also observed with N-phenyl-p- ...