Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes

作者: Lucio Minuti , Aldo Taticchi , Eszter Gacs-Baitz , Assunta Marrocchi

DOI: 10.1016/S0040-4020(98)00642-5

关键词:

摘要: Abstract A one-pot high yielding route to 3,4-dihydro-1-(2H)-anthracenone (9) based on pressure Diels-Alder reaction is described. The synthesis of 3,4-dihydro-1-vinylphenanthrene (1) and 3,4-dihydro-1-vinylanthracene (2) reported. new synthetic two-step approach [5]phenacenes fluorenoanthracenes has been developed. It the arylethenes 1 2 with benzyne (13), 1,4-benzoquinone (14), 1,4-naphthoquinone (15) inden-1-one (17) aromatization cycloadducts. Structure analysis products by 1H 13C-NMR spectroscopy presented.

参考文章(21)
Aldo Taticchi, Francesco Fringuelli, Dienes in the Diels-Alder reaction ,(1990)
Eszter Gacs-baitz, Lucio Minuti, Aldo Taticchi, Short Synthetic Approach to Benzo[G]Cyclopenta[A]- Phenanthrenes and Benzo[G]-Indeno[A]Phenanthrenones Polycyclic Aromatic Compounds. ,vol. 8, pp. 213- 227 ,(1996) , 10.1080/10406639608048349
Lucio Minuti, Aldo Taticchi, Assunta Marrocchi, Eszter Gacs-Baitz, Diels-Alder reaction of 3,3′,4,4′-tetrahydro-1,1′-binaphthalene. One-pot synthesis of a pentahelicenebenzoquinone Tetrahedron. ,vol. 53, pp. 6873- 6878 ,(1997) , 10.1016/S0040-4020(97)00318-9
Frank B Mallory, Kelly E Butler, Amanda C Evans, Clelia W Mallory, Phenacenes: A family of graphite ribbons. 1. Syntheses of some [7]phenacenes by stilbene-like photocyclizations☆ Tetrahedron Letters. ,vol. 37, pp. 7173- 7176 ,(1996) , 10.1016/0040-4039(96)01618-8
Lucio Minuti, Hans W. Scheeren, Roberta Selvaggi, Aldo Taticchi, HIGH PRESSURE LEWIS-ACID CATALYZED DIELS-ALDER REACTIONS OF 3-METHYL-2-CYCLOPENTEN-1-ONE. A NEW CONSTRUCTION OF ANGULARLY METHYLATED HYDRINDANONES Synthetic Communications. ,vol. 22, pp. 2965- 2969 ,(1992) , 10.1080/00397919208021122
Francesco Fringuelli, Aldo Taticchi, Ernest Wenkert, DIELS-ALDER REACTIONS OF CYCLOALKENONES IN ORGANIC SYNTHESIS Organic Preparations and Procedures International. ,vol. 22, pp. 131- 165 ,(1990) , 10.1080/00304949009458194
Lucio Minuti, Aldo Taticchi, Eszter Gacs-Baitz, Assunta Marrocchi, High Pressure Diels-Alder Reactions of 2-Vinyl-3,4-Dihydronaphthalene. Synthesis of Cyclopenta[c]- and Indeno[c]Phenanthrenones. Tetrahedron. ,vol. 51, pp. 8953- 8958 ,(1995) , 10.1016/0040-4020(95)00504-2
Joel Selbin, The Chemistry of Oxovanadium(IV) Chemical Reviews. ,vol. 65, pp. 153- 175 ,(1965) , 10.1021/CR60234A001