Umsetzungen von Lactonen

Abstract

Aus den Produkten der Einwirkung des Phenylmagnesiumbromids auf das Lacton der 2, 4-Dimethylpentan-2, 4-diol-1-S~ure (I) war, wie der eine von uns vor l~ingerer Zeit mitteilen konnte, ein KSrper C19H~O~ ~ isoliert worden, ffir den die Struktur eines tertitiren Alkohols der Tetrahydrofuranreihe (lII) in Betracht gezogen wurde. Die Entstehung dieses KSrpers wurde durch Anhydrisierung des bei der Grignardschen Reaktion prim/it entstehenden Triols (II) erkl/trt: (I) (II) CH3\ C(OH)< C6H5 ___~ ,/C(OH). CH.,C(OH'I.

The Chemistry of Isatin.

“…A7-Methylisatin and A7-ethylisatin can be prepared most conveniently by alkylating isatin by means of methyl sulfate and ethyl sulfate, respectively (43,122,242,244).…”

“…3,3-Dichlorooxindole pentachloride are allowed to react slowly at room temperature the product is 3,3-dichloroóxindole (II) (153). A-Alkyl derivatives of isatin react with phosphoms pentachloride to give the 1-alkyl-3,3-dichlorooxindoles (78,118,241,244,303,378).…”

“…The reactions of isatin and its derivatives with Grignard reagents have been studied by Kohn and coworkers (238,239,242,243,244), by Myers and Lindwall (310), and by other workers (205,369,370,373,381,387,389) Grignard reagents isatin yields the corresponding 3-alkyl (or aryl)-3-hydroxyoxindoles (I). Kohn (243) found that when phenylmagnesium bromide and IV-methylisatin were allowed to react in equimolecular proportions the analogous l-methyl-3-phenyl-3-hydroxyoxindole (II) was obtained.…”

“…152,240,241,242,244,268,382,385,403). On the other hand Heller has proposed a quinhydrone structure (II) for isatide (174, h i b i t e d .…”

The Chemistry of Oxindole.

“…3-Alkyl-3-hydroxyoxindoles (IX) are readily prepared by the action of Grignard reagents on isatin (85,115,116,119,120,121,154,174,175,176,182,186,187). (For other syntheses of 3-phenyl-3-hydroxyoxindole see references 13 and R ---COH /CO NCH».…”