Reactions of N-methyl-N-nitrosotoluene-P-sulfonamide (MNTS) with 3,6-dibromocarbazole and its corresponding nitranion

Authors
Zhu, XQ Li, Q Lu, JM Li, Y He, JQ Cheng, JP
Citation
Xq. Zhu et al., Reactions of N-methyl-N-nitrosotoluene-P-sulfonamide (MNTS) with 3,6-dibromocarbazole and its corresponding nitranion, RES CHEM IN, 26(7-8), 2000, pp. 705-714
Citations number
27
Categorie Soggetti
Chemistry
Journal title
RESEARCH ON CHEMICAL INTERMEDIATES
ISSN journal
09226168 → ACNP
Volume
26
Issue
7-8
Year of publication
2000
Pages
705 - 714
Database
ISI
SICI code
0922-6168(2000)26:7-8<705:RON(W3>2.0.ZU;2-9
Abstract
Reaction of N-methyl-N-nitrosotoluene-p-sulfonamide (MNTS, 1) with 3,6-dibr omocarbazole (2) in dry acetonitrile gave N-methyl-p-toluenesulfonamide (4) and N-nitroso-3,6-dibromocarbazole (5), whereas with the corresponding nit ranion (3) gave N-(p-toluenesulfonyl)-3,6-dibromocarbazole (6). The results are rationalized in terms of direct nucleophilic substitution mechanism oc curring on respective sites. The effects of solvents and added metal ions a re also discussed.