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Volumn 12, Issue 8, 2010, Pages 1840-1843

A divergent mechanistic course of Pd(0)-catalyzed aza-claisen rearrangement and aza-rautenstrauch-type cyclization of N -allyl ynamides

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; IMINE; PALLADIUM;

EID: 77951185847     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100446p     Document Type: Article
Times cited : (48)

References (98)
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    • Although attempts were made, these reactions were too fast to allow NMR studies to be revealing of possible ynamido-allyl complexes even at 25 °C. Only the starting ynamide 7 and silyl ketenimine 9 (and amidine 10 if the reaction was run in the presence of an amine) were clearly on display spectroscopically.
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    • It is noteworthy that our work distinctly indicates that the N-to-C 1,3-Ts shift took place after the aza-Claisen rearrangement. Monitoring the thermal aza-Claisen rearrangement of 11 using NMR did not reveal any ketenimine 12, thereby suggesting the 1,3-Ts shift was very fast at 110 °C.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.