Stereochemistry of hindered benzophenones: synthesis and resolution of 3-carboxymethyl-2,2',4,4',6,6'-hexamethyl-3'-nitrobenzophenone

Narayanan, K. V. ; Selvarajan, R. ; Swaminathan, S. (1968) Stereochemistry of hindered benzophenones: synthesis and resolution of 3-carboxymethyl-2,2',4,4',6,6'-hexamethyl-3'-nitrobenzophenone Journal of the Chemical Society C Organic, 1968 . pp. 540-543. ISSN 0022-4952

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1968...

Related URL: http://dx.doi.org/10.1039/J39680000540

Abstract

3-Bromo-2,2',4,4',6,6'-hexamethyl-3'-nitro-, 2,2'4,5',6-pentamethyl-3-nitro-, 3-bromo-2,2',4,6-tetramethyl-5'-nitro-, and 2,2',4,4',6,6'-hexamethyl-3-methoxycarbonylmethyl-3'-nitro-benzophenone were prepared by Friedel-Crafts acylation. The last compound was hydrolysed to 3-carboxymethyl-2,2',4,4',6,6'-hexamethyl-3'-nitrobenzophenone, which was resolved by way of the brucine salt; this demonstrates for the first time the existence of optical isomerism in suitably substituted benzophenones because of steric interactions between the o- and o'-substituents.

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