ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Acylimines, III. The Reaction of Acylimonium Salts with Grignard ReagentsOrganometallic compounds add to the CN-double bond to acyclic acylimines and cyclic acylimonium salts without substituent to the carbon atom of the functional group (4a and 4n). 1-Oxo-2,3-diphenyl-1H-isoinodol-2-ium hexachloroantiomonate (4d) does not react with phenylmagnesium bromide, and 1-oxo-3-phenyl-1H-isoindol-2-ium salts 4c add phenylmagnesium bromide at the CO- and methylmagnesium iodide at the CN-double bond These results show that the reaction is strongly influenced by steric factors. The reaction of 4c and that of 9 with phenylmagnesium bromide yield the same products, indicating that 1-hydroxy-1,3-diphenyl-1H-isonidol (8) is an intermediate in both reactions.
Notes:
Während acyclische Acylimine und cyclische Acylimoniumsalze ohne substituent am Kohlen stoffatom der Funktionsgruppe (4a aud 4b) metallorganisch Verbindungen an der Cn-Doppelbindung addieren, reagiert 1-Oxo-2,3-diphenyl-1H-isoindol-2-ium-Salze 4c addieren Phenylmagnesiumbromid an der Co-Doppeldbindung, Methylmagnesiumjodid hingegen an der CN-Doppelbindung. Das deutet auf sterische Faktoren. Die Umsetzung des 3-Chlor-3-phenyl-1-isoindolinous (9) mit Phenylmagnesiumbromid entspricht der der salze 4c.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19741070124
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