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Intramolecular reactions of acyclic n-acyliminium ions II allyl silanes as nucleophiles

✍ Scribed by Henk Hiemstra; Hendrikus P. Fortgens; W.Nico Speckamp

Book ID
104228796
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
270 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Intramolecular reactions of acyclic N-acyliminium ions with ally1 silanes, induced by protic or Lewis acid, lead to 3-vinylpyrrolidines or %vinylpiperidines.

In the preceding communication we have described intramolecular reactions of acyclic N-acyl-. iminium ions with propargyl silanes'. In this paper we disclose our results on the use of ally1 silanes as nucleophiles. There are scme scattered reports in the literature on intramolecular electrophilic addition of acyclic N-acyliminium ions to simple olefins2, but detailed studies on scope and stereo-and regiochemistry are lacking. The intermolecular reaction between acyclic N-acyliminium ions and olefins is well-known, and shows the features of a pericyclic C4+21 cycloaddition reaction 374 .

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Intramolecular reactions of acyclic n-ac
Intramolecular reactions of acyclic n-acyliminium ions III silicon assisted cyclocondensation of glyoxylic esters to proline and pipecolic acid derivatives
✍ Hendrik H Mooiweer; Henk Hiemstra; Hendrikus P Fortgens; W.Nico Speckamp πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 267 KB

Cyclizations of acyclic N-acyliminium ions, generated from the adducts of formaldehyde, n-butyl glyoxylate or methyl glyoxylate with amines containing an ally1 or propargyl silane as terminator, lead to 3-ethenyl and 3-ethenylidene substituted pyrrolidines and piperidines, some of which are structur