Two new abnormal by-products of attempted Fischer-type bis-indolisation of cyclohexane-1,3-dione and dimedone

Abstract

<span style="font-size:13.5pt;mso-bidi-font-size:8.5pt; font-family:" times="" new="" roman";mso-fareast-font-family:"times="" roman";="" mso-ansi-language:en-us;mso-fareast-language:en-us;mso-bidi-language:ar-sa"="">An attempt to bring about the bis-indolisation of cyclohexane- 1,3-dione and dimedone separately by treatment with phenylhydrazine (two equiv.) in dry benzene in the presence of stoichiometric amounts (two equiv.) of phospho-rous trichloride furnishes, besides the corresponding bis-(phenylhydrazones), the respective 2-oxo-bis(phenylhydra-zones) as new by-products which have been identified by spectral analyses. A mechanism for the formation of the latter <span style="font-size:11.5pt;mso-bidi-font-size:6.5pt;font-family:HiddenHorzOCR; mso-hansi-font-family:" times="" new="" roman";mso-bidi-font-family:hiddenhorzocr;="" mso-ansi-language:en-us;mso-fareast-language:en-us;mso-bidi-language:ar-sa"="">has <span style="font-size:13.5pt;mso-bidi-font-size:8.5pt;font-family:" times="" new="" roman";="" mso-fareast-font-family:"times="" roman";mso-ansi-language:en-us;mso-fareast-language:="" en-us;mso-bidi-language:ar-sa"="">been proposed.</span></span></span>