+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Chemistry of 1-fluoro-2,3,4-triphenylcyclobutadiene dimers

, : Chemistry of 1-fluoro-2,3,4-triphenylcyclobutadiene dimers. Journal of Organic Chemistry 72(25): 9732-9735

The reaction of 2,4-dichloro-1,1-difluoro-3-phenyl-2-cyclobutene 1 with excess phenyllithium and subsequent transformations of the products have been reinvestigated. The phenyllithium reaction appears to proceed through the intermediacy of a fluorotriphenylcyclobutadiene 2 to produce a well-characterized dimeric trans-hexaphenyldifluorotricyclooctadiene 3a. Subsequent transformations of 3a gave a pentaphenyldihydrodifluoropentalene 4, which on acid hydrolysis formed a pentaphenyldihydropentalenone 5. When 3a was photolyzed in benzene, after purification, it afforded 6, an isomer of 5, probably by way of 7, an isomer of 4. Thermolysis of 3a also provided, in low yield, a substance believed to be a pentaphenylfluorophenanthrene 8. Along with isolation of 3a, and probably arising from a different isomer of the 3 family, was a pentaphenylfluorophenanthrene 9, which was suspected of being an isomer of 8. Single-crystal X-ray studies were used to derive structures for 4, 5, 6, and 9. Formation of the unusual and intriguing transformation products has at least been rationalized.


PMID: 17979294

DOI: 10.1021/jo701900k

Other references

Gastaldi, M.; Robaglia-Schlupp, A.; Massacrier, A.; Planells, R.; Cau, P., 1998: mRNA coding for voltage-gated sodium channel beta2 subunit in rat central nervous system: cellular distribution and changes following kainate-induced seizures. The cellular distribution of sodium channel beta2 subunit mRNA was examined in the central nervous system from adult Wistar rats using a non-radioactive in situ hybridization method with digoxigenin-labeled cRNA probes. The expression of the subun...

Emmerich, J.; Fiessinger, J.N., 1999: Stroke from traumatic arterial dissection. Lancet 354(9173): 160-160

Anonymous, 2012: A new upper Middle Ordovician–Lower Silurian drillcore standard succession from Borenshult in Östergotland, southern Sweden 2 Significance of ?13C chemostratigraphy. A total of 239 isotope samples are used for establishing the ?13C chemostratigraphy in the upper Middle Ordovician to Lower Silurian succession in the approximately 7 m long Borenshult drillcore. The study interval starts in the upper Darriwilian...

Lishko V.K.; Malysheva M.K.; Polyakova N.M., 1971: Interaction of sodium ion potassium ion atpase with ouabain. Ukrayins'kyi Biokhimichnyi Zhurnal 43(1): 17-24

Iwahashi, M.; Nakamori, M.; Nakamura, M.; Naka, T.; Ojima, T.; Iida, T.; Katsuda, M.; Ueda, K.; Yamaue, H., 2009: Evaluation of double tract reconstruction after total gastrectomy in patients with gastric cancer: prospective randomized controlled trial. The double tract (DT) method was compared with the Roux-en-Y (R-Y) method to identify the optimal reconstruction procedure after total gastrectomy for patients with gastric cancer. The DT reconstruction is as simple as the R-Y, and it can be safel...

Gillard, B.K.; Marksman, H.C.; Feig, S.A., 1977: Direct spectrophotometric determination of alpha-amylase activity in salive, with p-nitrophenyl alpha-maltoside as substrate. We describe a simple, direct kinetic method for determination of salivary alpha-amylase (1,4, alpha-D-glucan 4-glucanohydrolase, EC The assay makes use of a well-defined substrate, p-nitrophenyl alpha-maltoside, which is hydrolyzed by al...

Kaemmel T., 1984: Statistical study of absolute ages of Variscan granitoids in the Erzgebirge and Vogtland. ZFI - Mitteilungen 85: 262-271

Narbaev, Z.N., 1987: Redescription of the cyst nematode Heterodera cardiolata Kirjanova & Ivanova, 1969. H. cardiolata, originally described from Cynodon dactylon in Tadjikistan, is redescribed from nematodes found on the same host plant in several regions of Uzbek SSR and in the Chimkint region of the Kazakh SSR. H. cardiolata may be differentiated...

Graham, W.R.; Smith, J.B.; Mcfarlane, W.D., 1931: Results of a three years study of certain poultry rations as they affect the hatching power of hen eggs as well as the number of eggs laid. In feeding value, for egg production, fish meal, powdered buttermilk, beef scrap and tankage, ranked in the order named. Cod liver oil added to a combination of milk and fish scrap, of milk and beef scrap, or of milk and tankage, increased the hat...

Gash, D.M.; Collier, T.J.; Sladek, J.R., 1985: Neural transplantation: a review of recent developments and potential applications to the aged brain. Mammalian neural transplantation has recently been recognized to be a valuable technique for studying normal development and regeneration in the central nervous system. In addition, the ability of grafted neurons to reinnervate damaged regions of...