Atropisomerism in monopyrroles

SE Boiadjiev, DA Lightner

Index: Boiadjiev, Stefan E.; Lightner, David A. Tetrahedron Asymmetry, 2002 , vol. 13, # 16 p. 1721 - 1732

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Citation Number: 16

Abstract

As observed by NMR, iodopyrroles 1a and 1b (ethyl and methyl 3, 5-dimethyl-4-[(1′-iodo- 2′, 2′-dimethyl) propyl] pyrrole-2-carboxylate) and a variety of related derivatives with iodine replaced by methoxy 2, thiomethyl 3, acetic acid esters 4, propionic acid ester 5 or malonic esters 6 exhibit restricted rotation about the C (4) C (1′) bond due to the bulky tert- butyl group and an ortho effect from the sterically crowded 3, 5-dimethylpyrrole. Most of ...