Aromatic nucleophilic substitution. 11. Effects of ortho substituents on the rates of the smiles rearrangements of (. beta.-acetylamino) ethyl 2-X-4-Y-6-Z-1-phenyl ethers …

S Sekiguchi, I Ohtsuka, K Okada

Index: Sekiguchi,S. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 14 p. 2556 - 2560

Full Text: HTML

Citation Number: 4

Abstract

N-(P-acetyloxy) ethyl-(3, main product) and N-(/3-hydroxy) ethyl-2-X-4-nitro-6-2-anilines. The ethers (Id and le) rearrange more rapidly than la (X= Y= NO,, 2= H) by a factor of 55 and 1680, respectively, indicating that the steric effect plays an important role in the rearrangement. P-(Acetylarnino) ethyl2, 6-dinitro-l-phenyl (If, X= Z= NO,; Y= H) and 2, 4- dinitro-6-methyl-l-phenyl ethers (lg, X= Y= NO,; 2= CHJ rearrange much more slowly, ...