title: 1,3-Dipolar cycloaddition reactions of 1-(4-phenylphenacyl)-1,10-phenanthrolinium N-ylide with activated alkynes and alkenes.
abstract: The 3+2 cycloaddition reaction of 1-(4-phenylphenacyl)-1,10-phenanthrolinium ylide 4 with activated alkynes gave pyrrolo[1,2- 4a][1,10]phenanthrolines 6a-d. The "one pot" synthesis of 6a,b,d from 4, activated alkenes, Et(3)N and tetrakis-pyridine cobalt (II) dichromate (TPCD) is described. The helical chirality of pyrrolophenanthrolines 6b-d was put in evidence by NMR spectroscopy.
authors.affiliation: Centre of Organic Chemistry C. D. Nenitzescu, Romanian Academy, Spl. Independentei 202B, Bucharest 060023, Romania. fdumitra@cco.ro
authors.forename: F
authors.initials: F
authors.lastname: Dumitrascu
authors.forename: M R
authors.initials: MR
authors.lastname: Caira
authors.forename: C
authors.initials: C
authors.lastname: Draghici
authors.forename: M T
authors.initials: MT
authors.lastname: Caproiu
authors.forename: A
authors.initials: A
authors.lastname: Badoiu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D008954:Models, Biological; D010618:Phenanthrolines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C526123:1-(4-phenylphenacyl)-1,10-phenanthrolinium N-ylide; D000480:Alkynes; D003516:Cycloparaffins; D006571:Heterocyclic Compounds; D010618:Phenanthrolines