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N-Acyliminium cyclizations via reversible 2-aza-cope rearrangements

โœ Scribed by Hugo Ent; Henk de Koning; W.Nico Speckamp


Book ID
104233306
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
183 KB
Volume
26
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The existence of a reversible 2-aza-Cope rearrangement in cyclizations of N-acyliminium ions derived from I'-and 2'-vinyl-N-(3'-butenyl)-5-hydroxy-2-pyrrolidinones is established.

Substituent effects in the rearrangement of N-acyliminium ions of the 2-aza-1,5-hexadienyl type A have previously been described in reports from our laboratory' and the Hart group2.


๐Ÿ“œ SIMILAR VOLUMES


The 2-aza-cope N-acyliminium cyclization
โœ Hugo Ent; Henk de Koning; W.Nico Speckamp ๐Ÿ“‚ Article ๐Ÿ“… 1983 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 213 KB
N-acyliminium ions: detection of a hidde
โœ David J. Hart; Yeun-Min Tsai ๐Ÿ“‚ Article ๐Ÿ“… 1981 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 184 KB

A 2-aza-Cope rearrangement underlying the more typical reactions of N-acyl-Z-aza-\_I\_\_\_\_\_\_ 1,5-hexadienes has been detected using triethylsilane as an acyliminium ion trap. Hetero-Cope rearrangements have previously been reported for substituted 2-aza-1,5-hexadienes 1 and their iminium ion co

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HCmH-ring closures of OH-lactams 7 possessing an ally1 substituted alkene function solely afford pyrrolizidines 8 and-2 in high yield via 2-aza-Cope rearrangent and ensuing cl-acyliminium cyclisation.