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Synthesis of 9,10–Dihydro–9,10–propanoanthracen–12–ones Substituted at the Bridgehead
Author(s) -
Martin H.,
Hoffmann R.,
Karama Usama
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921251228
Subject(s) - chemistry , bromine , adduct , sonication , stereochemistry , solvent , copper , zinc , medicinal chemistry , organic chemistry , chromatography
A variety of 9,10–dihydro–9,10–propanoanthracen–12–ones 1–11 has been prepared from anthracenes 15–23 , α,α′‐dibromo ketones 12–14 and zinc/copper couple by using dioxane as solvent and ultrasonication at 15–20°C. 2,2,4,4–Tetrabromoacetone ( 12 ) afforded cycloadducts, in which the two bromine atoms at C–11 and C–13 are introduced stereoselectively cis and adopt a syn diaxial instead of a cis ‐diequatorial position (5 examples). Even the cis ‐configurated methyl groups in adducts 8, 9 and cis ‐ 11 adopt syn diaxial positions preferentially.