Acid Catalyzed Condensations. I. 1,3,5-Triarylbenzenes¹

Abstract

The preparation of a series of 1,3,5-triarylbenzenes from substituted acetophenones is described. The effect of solvent and concentration on the yield of product and the course of reaction is noted.

Palladium‐Catalyzed Regioselective Cyclotrimerization of Acetylenes in Supercritical Carbon Dioxide

“…This reaction is environmentally more friendly than the traditional reaction in organic solvents and shows potential utility in industry. The mechanism and ap- (11) 1.813(8), Cl(2)ϪC (7) 1.776(10), Cl(3)ϪC (12) 1.761(9), Cl(4)ϪC (9) 1.819(8), Cl (5)ϪC (6) 1.800(8), Cl(6)ϪC (8) 1.683(9), C(1)ϪC (2) 1.298(9), C(1)ϪC (6) 1.444(10), C(2)ϪC (7) 1.460(11), C(3)ϪC (9) 1.444(12), C(4)ϪC (5) 1.368(9), C(6)ϪH(6A) 0.9700, C(6)ϪH(6B), 0.9700, C(7)ϪH(7A) 0.9700, C(7)ϪH(7B) 0.9700, Cl (9)ϪC (10) (7)ϪH(7B) 108.7, C(5)ϪC(1)ϪC(2)ϪC (7) Ϫ179.4(8), C(6)ϪC(1)ϪC(2)ϪC (3) Ϫ179.2(8), C(6)ϪC (1)ϪC (5)ϪC(4) Ϫ179.7(9), C(2)ϪC(1)ϪC (5)ϪC(12) Ϫ178.9(10), C(2)ϪC(3)Ϫ C(9)ϪC(10) Ϫ120.5(10), C(4)ϪC(3)ϪC(9)ϪC(10)Ϫ124.9 (10) plications of the reaction are currently under investigation in our laboratory.…”

“…[9] 301, 287, 273, 259, 245, 229, 217, 187, 175, 159, 145, 133, 105, 91, 80, 69, 55, 43, 29. 1,3,5-Tri-tert-butylbenzene (2c): Solid, m.p. 70Ϫ73°C [10] 219,202,199,183,163,157,143,123,107,91,77,65,57,41,29 250,249,222,221,194,193,176,165,148,137,120,103,91,75,65,45,29 370, 366, 364, 337, 335, 333, 321, 319, 317, 299, 297, 295, 265, 261, 235, 211, 199, 181, 177, 163, 141, 128, 115, 103, 89, 76, 57, 51, 29. Crystal Data for 7: C 12 H 12 Cl 6 , M r ϭ 368.92, white crystal, grown from petroleum ether, monoclinic, space group P2 1 /n, a ϭ 13.1340(19), b ϭ 9.4866(13), c ϭ 13.6005(19) Å , β ϭ 112.771(2)°, V ϭ 1562. …”

Effect of Confined Spaces in the Catalytic Activity of 1D and 2D Heterogeneous Carbon‐Based Catalysts for Synthesis of 1,3,5‐Triarylbenzenes: RGO‐SO3H vs. MWCNTs‐SO3H

“…In 1953, Lyle reported first work using alcoholic hydrogen chloride for trimerization of different methyl ketones . After a few years, diverse rhodium complexes and TiCl 3 (OTf) catalyzed cyclotrimerization of methyl ketones.…”

“…In 1953, Lyle reported first work using alcoholic hydrogen chloride for trimerization of different methyl ketones. [18] After a few years, diverse rhodium complexes [19] and TiCl 3 (OTf) [20] catalyzed cyclotrimerization of methyl ketones. A method for the synthesis of 1,3,5-triarylbenzenes using TiCl 4 was reported by Li and co-workers.…”

Efficient Conversion of Acetophenones into 1,3,5-Triarylbenzenes Catalyzed by Bismuth(III) Trifluoromethanesulfonate Tetrahydrate

“…3 Their preparation via triple condensation of aryl methyl ketones has been regarded as a useful general method and has been extensively studied. 4 Acid catalysts such as dry HCl, 4,5 PTSA/SnCl 4 , 6 SiCl 4 , 7 TiCl 4 8 , TiCl 3 (OTf), 9 and solid acid catalysts 10 are widely used for this transformation. However, these methods often involve the use of large amounts of catalysts which are expensive, moisture sensitive, toxic, and produce unsatisfactory yields, especially with ortho-substituted acetophenones.…”