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A facile synthesis of indoline-systems involving an intramolecular cyclisation via arylcarbenes

✍ Scribed by R. Garner

Publisher: Elsevier Science
Year: 1968
Tongue: French
Weight: 170 KB
Volume: 9
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)75592-4

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✦ Synopsis

p-Toluenesulphonylhydrazones of benzaldehydes with an ortho-t-amine -_ substituent, e.g. VI, decompose rapidly by the action of sodium methoxide in boiling diglyme (diethylene glycol dimethyl ether) to yield indolines, e.g. XII, in ca. 40% yield. This new application of the Bamford-Stevens reaction (1) undoubtedly involves an intramolecular insertion of the intermediate arylcarbene (Ar-CH) rather than the alternative carbonium ion

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