Premium
5‐Methoxyfuroxano[3,4‐ d ]pyrimidine: a highly reactive neutral electrophile
Author(s) -
Remennikov Grigoriy Ya.,
Kempf Bernhard,
Ofial Armin R.,
Polborn Kurt,
Mayr Herbert
Publication year - 2003
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.606
Subject(s) - chemistry , electrophile , nucleophile , pyrimidine , reaction rate constant , medicinal chemistry , yield (engineering) , ethylene , kinetic energy , computational chemistry , kinetics , organic chemistry , stereochemistry , thermodynamics , catalysis , physics , quantum mechanics
5‐Methoxyfuroxano[3,4‐ d ]pyrimidine ( 3 ) reacts with electron‐rich arenes and ethylene derivatives 4 at C‐7 to yield 7‐substituted 6,7‐dihydro‐5‐methoxyfuroxano[3,4‐ d ]pyrimidines ( 5 ). Kinetic investigations of these reactions showed that the rate constants can be described by the correlation equation log k (20 °C) = s ( N + E ). The electrophilicity parameter E ( 3 ) = −8.37 derived from the second‐order rate constants indicates that 3 reacts with nucleophiles of N ≥ 3. Copyright © 2003 John Wiley & Sons, Ltd.