Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 4, Pages 1441-1444Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508804
Keywords
diazo compounds; heterocycles; hydrazones; rearrangements; ring expansion
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Funding
- Science & Technology Department of Sichuan Province [2013JY0095]
- Education Department of Sichuan Province [15CZ0016]
- Innovative Research Team in College of Sichuan Province [14TD0016]
- NSFC [21572183]
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A new metal-free, ring-expansion reaction of six-membered N-sulfonylimines with unstable diazomethanes, generated in situ from the N-tosylhydrazones, has been developed. This reaction delivers valuable seven-membered enesulfonamides by a Tiffeneau-Demjanov rearrangement and intramolecular proton transfer tautomerization process. Moreover, this ring-expansion reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using aryl aldehydes, without the need to isolate the N-tosylhydrazone.
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