Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
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A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes

Mark York A B C D and Adriana Edenharter A

A CSIRO Materials Science and Engineering, Clayton, Vic. 3169, Australia.

B Cooperative Research Centre for Polymers, Notting Hill, Vic. 3168, Australia.

C Advanced Polymerik Pty Ltd, Notting Hill, Vic. 3168, Australia.

D Corresponding author. Email: mark.york@csiro.au

Australian Journal of Chemistry 66(2) 172-177 http://dx.doi.org/10.1071/CH12435
Submitted: 25 September 2012  Accepted: 9 November 2012   Published: 28 November 2012

Abstract

A continuous-flow process for the synthesis of several known and previously unreported spirooxazine photochromic dyes is reported. The process proceeds via an initial copper catalysed addition of substituted anilines to naphthalene-1,2-dione. This is followed by reaction with 1,3,3-trimethyl-2-methyleneindoline in the presence of hydroxylamine hydrochloride to give the desired spirooxazine products. The photochromic dyes were then cast into lenses to allow a preliminary evaluation of their properties.


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