THE MECHANISM OF CYCLIZATION OF 1-ETHYL-2-NITROBENZENE TO GIVE 3-METHYLANTHRANIL IN TRIFLUOROMETHANESULFONIC ACID - EVIDENCE FOR AN INTRAMOLECULAR HYDROGEN-TRANSFER

Authors
AUSTIN RP RIDD JH
Citation
Rp. Austin et Jh. Ridd, THE MECHANISM OF CYCLIZATION OF 1-ETHYL-2-NITROBENZENE TO GIVE 3-METHYLANTHRANIL IN TRIFLUOROMETHANESULFONIC ACID - EVIDENCE FOR AN INTRAMOLECULAR HYDROGEN-TRANSFER, Perkin transactions. 2, (6), 1993, pp. 1229-1232
Citations number
17
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Perkin transactions. 2 → ACNP
ISSN journal
03009580
Issue
6
Year of publication
1993
Pages
1229 - 1232
Database
ISI
SICI code
0300-9580(1993):6<1229:TMOCO1>2.0.ZU;2-P
Abstract
Deuterium labelling has been used to show that the cyclisation in trif luoromethanesulfonic acid of 1 -ethyl-2-nitrobenzene to 3-methylanthra nil does not proceed through an equilibrium concentration of the aci-f orm of the substrate. Instead, the rate-determining step appears to in volve the intramolecular transfer of hydrogen from the alpha-carbon at om to one of the oxygen atoms of the protonated nitro group. This conc lusion is supported by semi-empirical molecular orbital calculations.