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Deuterated dicondensed indolinobenzospiropyran formed from the reaction of Fischer base-d(2) and salicylaldehyde: Mechanism involving a carbinol intermediate
- Issue Date
- 1월-2009
- Publisher
- ELSEVIER SCI LTD
- Keywords
- Dicondensed indolinobenzospiropyran; Carbinol intermediate; Merocyanine intermediate; Michael-type addition; Simultaneous reaction pathway; Consecutive reaction pathway
- Citation
- DYES AND PIGMENTS, v.80, no.1, pp.26 - 29
- Indexed
- SCIE
SCOPUS
- Journal Title
- DYES AND PIGMENTS
- Volume
- 80
- Number
- 1
- Start Page
- 26
- End Page
- 29
- ISSN
- 0143-7208
- Abstract
- From the deuterium content (x-value) of deuterated molecules obtained from the reaction of an excess of Fischer base-d(2) with salicylaldehydes, it is found that the formation of the dicondensed indolinobenzospiropyrans occurred via a carbinol intermediate, rather than an open merocyanine form of spiropyran. H-1 NMR behavior supported this proposed mechanism, indicating that a carbinol intermediate was simultaneously, and not consecutively, formed prior to the transformation to both spiropyrans and dicondensed indolinobenzospiropyran. (C) 2008 Elsevier Ltd. All rights reserved.
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