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Synthesis and examination of transmission of the substituent effect in dimethyl 4-X-2,3-thiophenedicarboxylates

P. Hrnčiar and M. Struhárik

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, 842 15 Bratislava

 

Abstract: Dimethyl 4-X-2,3-thiophenedicarboxylates (X = NH2, NHCOCH3, H, CI, Br, I, CN, NO2 ) were synthesized and their i.r. and 1H-n.m.r. spectra were measured. The correlations between the respective v(C=0)I, v(C=0)II and chemical shift (p.p.m.) of the proton at C-5, and constants of substituents were studied. Best correlativities for transmission in ortho position 3—4 with σ+m constants and in ortho position 2—3 with σp constants were ascertained.

Full paper in Portable Document Format: 363a401.pdf

 

Chemical Papers 36 (3) 401–409 (1982)

Thursday, July 29, 2021

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