| Summary: | 碩士 === 國立臺灣大學 === 化學研究所 === 89 === Abstract
A series of (E)-2-(1-indanylidenememethyl)thiophene (1,2) , (E)-1- benzylideneindan (3), (E)-2-(1-indanylidenemethyl)furan (4) and corres- ponding stilbene type compounds (5,6,7) are synthesized by Wittig -Horner reaction.
A novel acid-catalyzed photochemical [1,3] hydrogen shift reaction is reported with very good yields (90~95%), and products are the decon- jugated, tautomerized benzylindene type compounds (8,10,11,12,13).
Semi-empirical PM3 type calculation is also carried out to elucidate the electron density, most stable conformation of the intermediates and the results serve to explain the possible reaction mechanism.
Compounds (8-13) can be converted back to the starting compounds simply by heating the solution in the presence of protic acids.
Thus this system represents a reversible photochromic reaction system. Plausible reaction mechanism is proposed for this novel tautomerization reaction.
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