COMPOUNDS OF THE Β-Tetralone SERIES

Synthesis of new chlorine-substituted derivatives of 2-tetralone

“…6-Chloro-2-tetralone (1).-A solution of p-chlorophenylacetyl chloride (46 g, 0.24 mol) in carbon disulfide (500 ml) was added dropwise with vigorous mechanical stirring to a suspension of anhydrous aluminum chloride (61.2 g, 0.46 mol) in carbon disulfide (700 ml) at 5°. When addition was complete, ethylene gas was introduced through a sintered-glass inlet tube for a period of 5 hr, with the temperature being kept at 5-10°. The mixture was stirred overnight at room temperature, and then poured into a large beaker of crushed ice.…”

“…In the present Note, we should like to report the preparation of 6-chloro-2-tetralone (I), 7-chloro-2-tetralone (2), 5,7-dichloro-2-tetralone (3), and 6,7-dichloro-2tetralone (4) via the Darzens reaction,3 as modified by Burckhalter and Campbell.4 R 1, R=R" = H;R' = C1 2, R-R'=H;R" = C1 3, R = R" = C1;R' = H 4, R=H;R' = R" = CI Methods of synthesis of 2-tetralone and its substituted analogs have been reviewed recently. 5 The approach favored by most workers during the past 25 years has involved reduction of substituted 2-methoxynaphthalene derivatives with sodium in alcohol. Catalytic, electrolytic, and sodium-liquid ammonia reductions have also been reported.…”

Chiral Auxiliary Approach for Gold(I)‐Catalyzed Cyclizations

“…Apart from alcohols as O ‐nucleophiles, electron‐rich indoles could also be used as C ‐nucleophiles [20] . Finally, upon the cleavage of the chiral auxiliary it was possible to isolate a new class of highly enantioenriched β‐tetralone derivatives, which are valuable frameworks in organic synthesis [21] and pharmacologically relevant intermediates such as antidepressants [22] or benzomorphan analgesics [23]…”