Methanal Extrusion in ipso-Substitution Reactions of Hydroxymethylindoles*

Jeremy C. Dobrowolski; Kittiya Somphol; Mardi Santoso; Hung Duong; Christopher R. Gardner; Naresh Kumar; David StC. Black

doi:10.1071/CH17257

RESEARCH ARTICLE

Methanal Extrusion in ipso-Substitution Reactions of Hydroxymethylindoles*

Jeremy C. Dobrowolski ^A , Kittiya Somphol ^A , Mardi Santoso ^A , Hung Duong ^A , Christopher R. Gardner ^A , Naresh Kumar ^A and David StC. Black ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, The University of New South Wales, UNSW Australia, Sydney, NSW 2052, Australia.

^B Corresponding author. Email: d.black@unsw.edu.au

Australian Journal of Chemistry 70(11) 1188-1195 https://doi.org/10.1071/CH17257
Submitted: 12 May 2017 Accepted: 2 August 2017 Published: 29 August 2017

Abstract

A range of 3-hydroxymethylindoles undergo acid-catalysed reactions involving ipso-electrophilic substitution with the extrusion of methanal and the formation of diindolylmethane moieties. Both inter- and intramolecular processes lead to macrocyclic compounds 10 and 14.

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