Reactions of aza-ortho-xylylenes generated from 2,1-benzisothiazoline 2,2-dioxides.

✍ Scribed by Krzysztof Wojciechowski

• Book ID: 104204408
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 686 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)87205-7

✦ Synopsis

Thermal extrusion of SO2 from 2,1-knxisothiaxoline 2,2dioxides 2 leads to axa-ovtho-xylylenes 3, which depending on the substituents undergo various tmnsfonnations. Aza-crrbxylylencs substituted at the position 4,5, and 6 gave DiebAlder reactions with mateic acid derivatives 4 leading to cir-1,2,3,4-tetrahydroquinoline f3dicarboxylic acid derivatives 5 in high yields. 7-Substituted derivatives underwent [1,5] hydrogen shift leading to or&toluidine derivatives 9 and 10. Aza-wfho-xyly1ene.s generated from N-(4pentenyl) and N-(S-hexenyl) derivatives 11 gave products of intramolecular Dick-Alder reaction.

9 Cl H NO, 2

This reaction requires the E configuration on the imine double bond and this is the configuration of the primarily formed aza-orrho-xylylene 12. From these results can be drawn the conclusion that the isomerisation