3-Benzylimino-2-pyrrolidinones can be prepared in good yield by heating 3-chloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80 degrees C. An endo-dehydrohalogenation followed by a SN2' substitution on the intermediate allyl chloride, and finally a shift of the exo-double bond to Delta(3) with attendant tautomerization, appears to be the most probable reaction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones / Ghelfi, Franco; G., Ghirardini; Libertini, Emanuela; Forti, Luca; Pagnoni, Ugo Maria. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 40:(1999), pp. 8595-8597. [10.1016/S0040-4039(99)01798-0]
Easy approach to 3-benzylimino-2-pyrrolidinones from 3-chloro-4-chloromethyl-2-pyrrolidinones
GHELFI, Franco;LIBERTINI, Emanuela;FORTI, Luca;PAGNONI, Ugo Maria
1999
Abstract
3-Benzylimino-2-pyrrolidinones can be prepared in good yield by heating 3-chloro-4-chloromethyl-2-pyrrolidinones, benzylamine and NaI in THF at 80 degrees C. An endo-dehydrohalogenation followed by a SN2' substitution on the intermediate allyl chloride, and finally a shift of the exo-double bond to Delta(3) with attendant tautomerization, appears to be the most probable reaction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.
| File | Dimensione | Formato | |
|---|---|---|---|
|
30_TL_1999.pdf
Accesso riservato
Tipologia:
Versione dell'autore revisionata e accettata per la pubblicazione
Dimensione
141.01 kB
Formato
Adobe PDF
|
141.01 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris
