TY - JOUR
T1 - Effect of N-chloro Structure and 1-substituent on (σ-substitution (Addition-Elimination) in Pyrroles
AU - De Rosa, Michael
AU - Nieto, Gustavo Cabrera
AU - Gago, Fernando Ferrer
PY - 1989/10/1
Y1 - 1989/10/1
N2 - 1-Methylpyrrole was reacted with a number of different types of N-chloro derivatives, and (σ-substitution was observed only with N-chloroimides. It is proposed that there is a qualitative relationship between the pKaof the N-chloro precursor and the reaction path. The reaction of 1-substituted pyrroles (CH3, C6H5, C6H6CH2, CH3CO0, (CH3)3C, CH2—CHCH2, (C6H6)3C) with N-chlorosuccinimide in CHCl3/NaHCO3indicated that (σ-substitution was very sensitive to electronic factors, e.g. no reaction was observed with 1-acetylpyrrole. It was not as sensitive to steric effects, and only with 1-tritylpyrrole was σ-substitution not observed. Only chlorination was observed with pyrrole itself.
AB - 1-Methylpyrrole was reacted with a number of different types of N-chloro derivatives, and (σ-substitution was observed only with N-chloroimides. It is proposed that there is a qualitative relationship between the pKaof the N-chloro precursor and the reaction path. The reaction of 1-substituted pyrroles (CH3, C6H5, C6H6CH2, CH3CO0, (CH3)3C, CH2—CHCH2, (C6H6)3C) with N-chlorosuccinimide in CHCl3/NaHCO3indicated that (σ-substitution was very sensitive to electronic factors, e.g. no reaction was observed with 1-acetylpyrrole. It was not as sensitive to steric effects, and only with 1-tritylpyrrole was σ-substitution not observed. Only chlorination was observed with pyrrole itself.
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U2 - 10.1021/jo00283a032
DO - 10.1021/jo00283a032
M3 - Article
AN - SCOPUS:0000224636
SN - 0022-3263
VL - 54
SP - 5347
EP - 5350
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 22
ER -