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Halogenation of Xanthenyl and Thioxanthenylallenes

✍ Scribed by Nadia Fouad Abdul-Malik; Sami Bassili Awad; Afly Badie Sakla

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
385 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Reactions of acids with vinylidenexanthenes (or thioxanthenes) 1 and 9‐methoxy‐9‐vinylxanthenes (or thioxanthenes) 8 give xanthene‐ (or thioxanthene‐) 9‐spiro‐1′‐indenes 7. With bromine or sulfuryl chloride they give the corresponding 2′‐halogenoxanthene‐ (or thioxanthene‐)9‐spiro‐1′‐indenes 5. Formation of such derivatives depends on preferential attack of the reagents on allenes 1 to give initially xanthylium (or thioxanthylium) ions 3 which cyclize. One π bond of the allenes 1 can be selectively reduced in acid media. Chemical and spectral evidence for these routes are presented.

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