Synthesis Of Tetralins Research Articles

Effect of Different Al2O3 Supports on the Synthesis of Tetralin by Selective Catalytic Hydrogenation of Naphthalene

Different Al2O3 carriers were synthesized by co-precipitation and sol-gel method. From them, 4%NiO-20%MoO3/Al2O3 catalysts were prepared by incipient wetness impregnation. The catalysts were characterized by X-ray diffraction analysis (XRD), N2 adsorption-desorption, NH3-temperature programmed desorption (TPD) and H2-temperature programmed reduction (TPR) and subsequently used for selective hydrogenation of naphthalene to high-value tetralin. The results showed that Ni-Mo/so-ge Al2O3 (900) exhibited better catalytic performance than Ni-Mo/commercial Al2O3, achieving 99.56% naphthalene conversion and 99.43% tetralin selectivity.

Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

This report describes the stereoselective synthesis of 3-azido-tetralins, -chromanes, and -tetrahydroquinolines via a tandem allylic azide rearrangement/Friedel-Crafts alkylation. Exposure of allylic azides with a pendant trichloroacetimidate to catalytic quantities of AgSbF6 proved optimal for this transformation. This cascade successfully differentiates the equilibrating azide isomers, providing products in excellent yield and selectivity (>25 examples, up to 94% yield and >25:1 dr). In many cases, the reactive isomer is only a trace fraction of the equilibrium mixture, keenly illustrating the dynamic nature of these systems. We demonstrate the utility of this process via a synthesis of hasubanan.

ChemInform Abstract: Synthesis of Tetralin and Chromane Derivatives via In‐Catalyzed Intramolecular Hydroarylation.

AbstractIn(OTf)3 is demonstrated to be an effective catalyst for the cyclization of different ω‐aryl‐1‐alkenes.

Synthesis of tetralin and chromane derivatives via In-catalyzed intramolecular hydroarylation

In(OTf) 3 was found to be an effective catalyst for the cyclization of ω-aryl-1-alkenes to form tetralin and chromane derivatives. Compared with the known Ru-catalyzed version, the In-catalyzed intramolecular cyclization was found to give higher yields and cleaner reactions in some cases. The use of cheaper indium salts instead of the expensive noble metal Ru can be advantageous when the reaction is run on a large scale.

A New, Safe and Convenient Procedure for Reduction of Naphthalene and Anthracene: Synthesis of Tetralin in a One‐Pot Reaction.

AbstractFor Abstract see ChemInform Abstract in Full Text.

A new, safe and convenient procedure for reduction of naphthalene and anthracene: synthesis of tetralin in a one-pot reaction

Reduction of naphthalene and anthracene with sodium and tert-butyl alcohol gave 1,4-dihydronaphthalene and 9,10-dihydroanthracene respectively in high yields at room temperature (r.t.) as the sole products. The synthesis of tetralin from naphthalene was carried out in a one-pot reaction via 1,4-dihydronaphthalene. The reduced products were easily isolated.

Studies toward the total synthesis of hibarimicinone. Progress on the assembly of the AB- and GH-ring systems

Studies directed towards the synthesis of the AB- and GH-ring systems of hibarimicinone are described. The synthesis of tetralin 3 was accomplished in three steps (43% overall yield) from benzoquinone and resolved using a Lipase-mediated resolution to >92% ee. Key reactions developed en route to the AB/GH ring systems of hibarimicinone include a dimethyl dioxirane oxidation for stereocontrolled introduction of the C(14) and C(14′) hydroxyl groups and the stereoselective addition of a n-propylcerium dichloride to ketone 13 to give diol 15 .

A Novel Method for the Stereoselective Synthesis of Tetralins and Indanes

Heavily-substituted 1-aryltetralins and 1-arylindanes were prepared in a highly stereoselective manner using a two-step sequence. Addition of t-butyl benzyl sulfoxides to unsaturated carbonyl compounds gave conjugate adducts with high diastereoselectivity. Treatment of the adducts with SnCl 4 generated benzyl carbocations which reacted intramolecularly with suitably-positioned aromatic rings to give tetralins and indanes, again with high diastereoselectivity.