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Syntheses and thermal reactions of 2-alkyl(or aryl)-1-benzoyl-3,4-dihydro-2-thianaphthalenes

✍ Scribed by Mikio Hori; Tadashi Kataoka; Hiroshi Shimizu; Akihiko Tomoto

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 266 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81978-x

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✦ Synopsis

1-Benzoyl-2-methyl-3,4-dihydro-2-thianaphthalene (4a) underwent novel intermolecular 1,4-rearrangement in refluxing toluene to give an enol ether 5z while rearrangement of 2-phenyl derivative 4e proceeded intramolecularly in refluxing xylene to afford a 1,4-rearranged enol ether 5b. 5 the other hand, ylides 4a-e were refluxed in alcohols to afford some ring-opened products 10_12. A large number of benzoyl-stabilized sulfur ylides have been synthesized and their reactivities have been investigated in past two decades. Thermal [2,3]sigmatropic rearrangement' and Stevens-type 1,2_rearrangement 2) of these ylides are well-known, however despite the facile enolization of the carbonyl group, 394) the 1,4_rearrangement of S-substituent to the carbonyl oxygen atom has not been found.

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