CYCLOPROPANONE EQUIVALENTS FROM 3-CHLOROPROPIONIC ACID. USE OF 1-PIPERIDINO-1-TRIMETHYLSILYLOXYCYCLOPROPANE IN SYNTHETIC APPLICATIONS
1-Piperidino-1-trimethylsilyloxycyclopropane and the corresponding 1-hydroxy-1-piperidinocyclopropane, conveniently prepared from the piperidide of 3-chloropropionic acid, react as cyclopropanone equivalents with various nucleophiles.Use of these derivatives in the formation of pyrroles, pyrrolines and pyrrolizidines is described.The rearrangement of dicyclopropyl ketimines is explored.
Wasserman, Harry H.,Dion, Robert P.,Fukuyama, James
p. 3203 - 3216
(2007/10/02)
REARRANGEMENT OF 1-PIPERIDINOCYCLOPROPYL KETIMINES. A SYNTHESIS OF 2-SUBSTITUTED PYRROLES
On heating 1-(N-piperidino)cyclopropyl ketimines with HBF4, rearrangement to 2-substituted pyrroles takes place.
Wasserman, Harry H.,Dion, Robert P.,Fukuyama, James M.
p. 629 - 631
(2007/10/02)
ACID-CATALYZED THERMOLYSIS OF DICYCLOPROPYL KETIMINES. SUBSTITUENT EFFECTS ON THE COURSE OF THE REARRANGEMENT
On thermolysis with ammonium halides, dicyclopropyl ketimines yield cyclopropyl pyrrolines resulting from SN2 ring-opening by the nucleophilic halide.In the absence of a nucleophilic counterion, the acid-catalyzed thermolyses lead to pyrroles if there can be stabilization of cationic intermediates by an electron-releasing substituent.
Wasserman, Harry H.,Dion, Robert P.
p. 3409 - 3412
(2007/10/02)
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