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Diels-Alder reactions of diaryl thioketones with dienophiles

✍ Scribed by Jochen Rapp; Rolf Huisgen

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 679 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(96)01069-1

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✦ Synopsis

Thiobenzophenone and its 4,4'-dichloro derivative combine as dienes (C= S + aromatic CC bond) with dimethyl acetylenedicarboxylate, methyl propiolate, dicyanoacetylene, and cyclooctyne furnishing lH-2-benzothiopyrans 10, 11, 13, 14, the primary [4+2] cycloaddition is followed by 1,3 prototropy. In the case of the strained (Ej-cyclooctene as a dienophile, the initial nonaromatic cydoadducts 19 were isolated and rearomatized by base catalysis. -In the MS of the VI-2-benzothiopyrans, M+ and [M+ -Ar] are preeminent, both as results of benzylic cleavage.

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