The Journal of Organic Chemistry

Synthesis of acylpyrroles via. alpha.-(dimethylamino)-. alpha.-pyrrolylacetonitriles

BL Bray, JM Muchowski

Index: Bray, Brian L.; Muchowski, Joseph M. Journal of Organic Chemistry, 1988 , vol. 53, # 26 p. 6115 - 6118

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Citation Number: 23

Abstract

The'H NMR spectra (Table I, supplementary material) of these salts indicate that they exist in the anti conformation since the iminium proton is coupled to H-4 (J= 0.6-0.7 Hz) but not to H- 5. This is unlike most pyrrole-2-carboxaldehydes for which the syn conformer predominates at room temperature (JCH0, HS= 1 Hz) but analogous to that observed for certain 1- acylpyrrole-2-carboxaldehydes (see ref 3, pp 286-289, 474-475). It is also noteworthy that ...