5385-36-4

Usage

InChI:InChI=1/C16H16/c1-2-15-10-8-13-4-6-14(7-5-13)9-11-16(3-1)12-15/h1-7,12H,8-11H2

Upstream product

• 51760-18-0 8-Brom-<2.2>-metaparacyclophan 
• 145223-49-0 5-tert-Butyl<2.2>metaparacyclophane 
• 1633-22-3 [2.2]Paracyclophan 
• 22176-78-9 <2.2>Metaparacyclophane-1,9-diene 
• 85892-27-9 <3.3>metaparacyclophane-2,11-dione 
• 626-15-3 1,3-bis-(bromomethyl)benzene 
• 51760-02-2 18-Bromo-3,11-dithia-tricyclo[11.2.2.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 3,3,11,11-tetraoxide 
• 7215-80-7 3,11-Diaza-tricyclo[11.2.2.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 
• 145223-45-6 6-tert-Butyl-2,11-dithia<3.3>metaparacyclophane 2,2,11,11-tetraoxide 
• 145223-41-2 6-tert-Butyl-2,11-dithia<3.3>metaparacyclophane 
• 64726-28-9 5-tert-butyl-1,3-bis(bromomethyl)benzene 
• 59395-13-0 1,3-Phenylenebis(methylene)selenocyanate 
• 117632-86-7 3,11-Dinitroso-3,11-diaza-tricyclo[11.2.2.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 
• 85539-79-3 3,11-Diselena-tricyclo[11.2.2.1^5,9]octadeca-1⁽¹⁶⁾,5,7,9⁽¹⁸⁾,13⁽¹⁷⁾,14-hexaene 

Downstream Products

• 100-42-5 styrene 
• 106-42-3 para-xylene 
• 694-87-1 benzocyclobutene 
• 108-38-3 m-xylene 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 4960-53-6 1-(3-methylphenyl)-2-(4-methylphenyl)ethane 

Relevant academic research and scientific papers

Alternative general synthetic routes to [2.2]cyclophanes and [3.2]cyclophanes from [3.3]cyclophane-2,11-diones by photodecarbonylation, and a structural study of [3.2]metacyclophanes

Photodecarbonylation of [3.3]cyclophane-2,11-diones, which are readily prepared by TosMIC coupling, affords [2.2]cyclophanes in high yield. This method also provides a general synthetic method for [3.2]cyclophan-2-ones by taking advantage of the fact that this photochemical reaction proceeds in a stepwise manner through [3.2]cyclophan-2-ones. A series of [2.2]cyclophanes, [3.2]cyclophanes, and [3.3]cyclophanes can thus be made available from the common precursor [3.3]cyclophane-2,11-diones. In sharp contrast to the preferred syn geometry of [3.3]metacyclophanes, [3.2] metacyclophanes adopt anti geometries and the aryl ring inversion process is observed by variable-temperature 1H NMR spectroscopy. In the crystalline state, the two aryl rings of anti-[3.2]metacyclophanes are almost parallel in spite of the unsymmetrical bridge length; they overlap only at the C-9 and C-17 positions, and the transannular distances are shorter than the corresponding distances in [3.3]metacyclophane-2,11-dione.

A new synthetic method of [2.2]cyclopbanes from [3.3]cyclophane-2,11- diones via photodecarbonylation

Photoirradiation of [3,3]cyclophane-2,11-diones with a high-pressure Hg lamp in benzene provides the corresponding [2,2]cyclophanes in high yields along with [3,2]-cyclophane-2-ones.

Medium-sized Cyclophanes. Part 18. 5-tert-Butyl-8-substituted Metaparacyclophanes: Preparation, X-Ray Diffraction Studies, and their Treatment with Lewis Acids in Benzene

The preparation of various 8-substituted 5-tert-butylmetaparacyclophanes 8 using the sulfur method, and X-ray diffraction studies of dithiametaparacyclophanes 6 and 8-methylmetaparacyclophane 1b, are described.AlCl3-MeNO2-catalysed trans-te

A NEW SYNTHETIC METHOD OF CYCLOPHANES

Diazacyclophanes were converted to the correspondingcyclophanes via their N-nitroso derivatives by reductive extrusion of nitrogens.This reaction is simple, clean and mild, and may be an alternative synthetic way of cyclophanes.

New Synthetic Method of Cyclophanes via Diselenacyclophanes

Syntheses of cyclic diselenides through diselenolates and the following deselenation reactions by means of three ways were studied.The preparation of the cyclic diselenides in the presence of excess sodium borohydride gave thirty-eight diselenides containing diselenacyclophanes and alicyclic diseleno compounds in high yields in addition to two triple-bridged selenacyclophanes.Photodeselenation of the diselenides in tris(dimethylamino)phosphine afforded series of cyclophanes in much higher yields than those of the other two methods, i.e. benzyne-Stevens rearrangement/Raney nickel hydrogenolysis and pyrolytic deselenation at ca. 650 deg C.The present study demonstrates that the photodeselenation method combined with the synthesis of their precursor diselenides, is much superior to the conventional dechalcogenation methods.

SYNTHESIS OF CYCLOPHANES BY PHOTODESELENATIVE RINGCONTRACTION

Several cyclophanes were prepared by photodeselenation of diselenacyclophanes with hexamethylphosphorous triamide in excellent yields, compared with the other chalcogen-atom extrusion methods.

DESELENATION OF DISELENACYCLOPHANES - A NEW SYNTHETIC METHOD OF CYCLOPHANES-

Several diselenacyclophanes were prepared by coupling of bisselenocyanates and bis(bromomethyl)benzenes in good yields.The benzyne Stevens rearrangement-Raney Ni hydrogenolysis method gave good yields of double- and triple-layered cyclophanes from the diselenides, though the flash pyrolysis method gave them in low yields.