ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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 = NH_2, 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 σ_p constants were ascertained.

Full paper in Portable Document Format: 363a401.pdf

Chemical Papers 36 (3) 401–409 (1982)