5‐Methoxyfuroxano[3,4‐ d ]pyrimidine: a highly reactive neutral electrophile | Zendy

Remennikov Grigoriy Ya. | Zendy; Kempf Bernhard | Zendy; Ofial Armin R. | Zendy; Polborn Kurt | Zendy; Mayr Herbert | Zendy

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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.

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