100367-30-4

Upstream product

• 390409-98-0 6,7-diiodo-1,2,3,4-tetraphenylnaphthalene 
• 1633750-72-7 (phenyl)(3-trimethylsilyl-5,6,7,8-tetraphenyl-2-naphthalen-yl)iodonium triflate 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 636-31-7 1,2,4,5-tetraiodobenzene 
• 501-65-5 diphenyl acetylene 
• 445483-84-1 octaphenylanthraquinone 
• 91477-70-2 1,5-diamino-1,5-dihydrobenzo<1,2-d:4,5-d'>bistriazole (DABT) 

Relevant academic research and scientific papers

Octaphenylbiphenylene and dodecaphenyltriptycene

Octaphenylbiphenylene, the expected dimer of tetraphenylbenzyne, has been prepared in low yield by diazotization of 3,4,5,6-tetraphenylanthranilic acid, and its X-ray structure has been determined. The X-ray structure of a second, abnormal dimer of tetrap

Improved and practical synthesis of [2,4,5-tris(trimethylsilyl)- Phenyl](phenyl)iodonium triflate and utilization as a 1,4-benzdiyne synthon

An efficient and improved method for preparing [2,4,5-tris(trimethylsilyl) phenyl](phenyl)iodonium triflate as a 1,4-benzdiyne synthon was developed by using phenyiodonium diacetate/boron triflouride diethyl etherate [PhI(OAc) 2/BF3 OEt2] reagent. The iodonium triflate generated 3,4-bis(trimethylsilyl)benzyne quantitatively to give cycloadducts with tetraphenylcyclopentadienone, furan and anthracene in high yields. These cycloadducts bearing two trimethylsilyl groups were transformed into the corresponding aryne precursors, which underwent subsequent cycloaddition reactions to afford polycyclic aromatic compounds such as 1,4-dihydro-1,4- epoxyanthracene, naphthotriazole, triptycene, and anthratriazole derivatives in good to high yields. The total reactions are formally considered as double cycloaddition reactions of 1,4-benzdiyne. This practical and useful formal benzdiyne strategy is described.

O-Dihaloarenes as aryne precursors for nickel-catalyzed [2 + 2 + 2] cycloaddition with alkynes and nitriles

o-Dihaloarenes acting as aryne precursors react with acetylenes and nitriles catalyzed by the NiBr2(dppe)/dppe/Zn system to give substituted naphthalene, phenanthridine or triphenylene derivatives depending on the reaction conditions in moderat

Coupling reaction of zirconacyclopentadienes with dihalonaphthalenes and dihalopyridines: A new procedure for the preparation of substituted anthracenes, quinolines, and isoquinolines

Reactions of tetraiodobenzene with zirconacyclopentadienes, which were conveniently prepared from two alkynes (or diynes) and zirconocene complexes, afforded 1,2,3,4-tetrasubstituted diiodonaphthalene derivatives in good isolated yields. These 1,2,3,4-tetrasubstituted diiodonaphthalene derivatives could be converted to 1,2,3,4,5,6,7,8-octasubstituted anthracene derivatives by reaction with a second zirconacyclopentadiene. When the two zirconacyclopentadienes were different, unsymmetrical anthracenes such as 1,2,3,4-tetraethyl-5,6,7,8-tetraphenylanthracene (68% isolated yield) were obtained. On the other hand, treatment of a 2,3-dihalopyridine such as 2-bromo-3-iodopyridine with zirconacyclopentadienes gave 5,6,7,8-tetrasubstituted quinoline derivatives in good to high yields. 3,4-Dihalopyridines such as 4-chloro-3-iodopyridine reacted with zirconacyclopentadienes to afford 5,6,7,8-tetrasubstituted isoquinoline derivatives in good to high yields.

Synthesis of 1,5-Diamino-1,5-dihydrobenzobistriazole (DABT) and Its Use as a 1,4-Benzadiyne Equivalent

Amination of 1,5-dihydrobenzobistriazole (9) gives the 1,5- and 1,7-diamino derivatives 3 and 10 both useful as 1,4-benzadiyne equivalents, as well as the 1,6 isomer 11 and the recyclable monoamino derivatives 12 and 13.Sixteen examples of the synthetic utility of DABT (3) with lead tetraacetate in bisannulations are described (Table 1).The aryne-trapping dienes include ester, halogen, and carbonyl functionality; often the reactions are quite regio- and stereoselective as a consequence of the stepwise nature of the annulations.