Aza-enamines-VII: Umpolung of the azomethine reactivity in the reaction of aldehyde hydrazones with sulfonyl isocyanates substituent effects
✍ Scribed by Rainer Brehme; Anke Klemann
- Book ID
- 104203013
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 475 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Abetraot. Sulfonyl isocyanates attaok the arylaldehyde N,Ndialkylhydrazones lmethine funotion 16a 3 at the nitrogen or oarbon of the azoing to the formation of the hexahydro-1,3,~triazine-2,4-diones 4-6 or arylglyo llc acid sulfonamide-N,N-dialkylhydrazone~ -perimental conditions the pos 14 (scheme 1 'Q; . Under equal ext on of the eleotrophilio attaok deoends on the oontribution of the dlpolar structures I~*I" determined by the eleotr n withdrawing or donating ootential of the substituents R !f and NRo. The normal reacti-;ity of the 7&N-funotlon Is desorlbed By eq.?, the ump'l$gg by eq.2. These different reaotlons correspond to the chemical shifts of the azomethine carbon atoms.
ill prepar~t& resp.10 1 omenolature and analytical data &XI .