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Norbornadiene

About: Norbornadiene is a research topic. Over the lifetime, 2389 publications have been published within this topic receiving 38603 citations.


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Journal ArticleDOI
TL;DR: In this paper, the authors describe a (1R)-(+)-camphor with 1,1-dimethylhydrazine 3a which with LiBu, followed by PPh2Cl, gives the corresponding compound 3c which has the Ph2P group in 3-exo position and the CN-NMe2 group in the Z configuration.
Abstract: Prolonged treatment of (1R)-(+)-camphor with 1,1-dimethylhydrazine gives (1R)-(+)-camphor dimethylhydrazone 3a which with LiBu, followed by PPh2Cl, gives the corresponding compound 3c which has the Ph2P group in 3-exo position and the CN–NMe2 group in the Z configuration. This new phosphine was quaternized with Mel to give a phosphonium salt and converted into the corresponding sulphide and oxide. Treatment of [M(CO)4(nbd)](M = Cr, Mo or W; nbd = norbornadiene) with 3c gives [[graphic omitted]NMe2)]4 in which the phosphine is chelated to the metal in a six-membered ring. However, when [Mo(CO)6] was heated with 3c in decane, isomerization around the CN bond occurred and the isomeric complex [[graphic omitted]NMe2)]5 was formed. When 4a was heated in diglyme it isomerized to 5. Proton and 31P-{1H} NMR and infrared data are given. Crystals of compound 3c are orthorhombic, space group P212121 with a= 1119.9(2), b= 1166.3(2), c= 1690.7(2) pm and Z= 4; final R factor 0.0443 for 3910 observed reflections. Crystals of complex 5 are orthorhombic, space group P212121, with a= 974.8(2), b= 1658.9(4), c= 1982.0(4) pm and Z= 4; R 0.0425 for 2991 observed reflections. The structure shows that the co-ordinated PPh2 group is in the 3-exo position whilst the CNNMe2 moiety is co-ordinated through the CN nitrogen, giving a five-membered co-ordinated ring and an unco-ordinated NMe2 group. The arrangement around the CN is E, i.e. the opposite to that in 3c.

10 citations

Journal ArticleDOI
TL;DR: In this paper, a new catalytic system based on palladium complex compounds for the unconventional allylation of norbornadiene with allylic esters of carboxylic acids is developed.
Abstract: A new catalytic system based on palladium complex compounds for the unconventional allylation of norbornadiene with allylic esters of carboxylic acids is developed. The structure of reaction products is determined and the factors affecting their ratio are found. Comparative analysis of the palladium and nickel catalytic systems is performed.

10 citations

Journal ArticleDOI
TL;DR: Perfluorocyclopentadiene as mentioned in this paper has been shown to participate in the Diels-Alder reaction as a diene in its thermal reactions with dimethyl acetylenedicarboxylate.
Abstract: Perfluorocyclopentadiene Partakes IN The Diels–Alder reaction (a) as a diene in its thermal reactions with dimethyl acetylenedicarboxylate (→ dimethyl 1,2,3,4,7,7-hexafluorobicylo[2,2,1]hepta-2,5-diene-5,6-dicarboxylate), ethylene (→ 1,2,3,4,7,7-hexafluorobicyclo[2,2,1]hept-2-ene), acetylene (→ 1,2,3,4,7,7-hexafluorobicyclo[2,2,1] hepta-2,5-diene), maleic anhydride (→ 1,2,3,4,7,7-hexafluorobicyclo[2,2,1]hept-2-ene-5,6-anhydride), butadiene (→ 1,2,3,4,7,7-hexafluoro-5-vinylbicyclo[2,2,1]hept-2-ene), norbornadiene (→ two stereoisomers of 3,4,5,6,12,12-hexafluorotetracyclo[6,2,1,13,6,02,7]dodeca-4,9-diene), trifluoronitrosomethane {→ perfluoro-(3-methyl-2-oxa-3-azabicyclo[2,2,1]hept-5-ene)}, but (b) as a dienophile when heated with anthracene [→ 9,10-dihydro-9,10-(11,12-hexafluorocyclopent-13-eno)anthracene], and (c) as both a diene (→ 1,7,8,9,10,10-hexafluorotricyclo[5,2,1,02,6]deca-3,8-diene) and a dienophile (→ 2,3,4,5,5,6-hexafluorotricyclo[5,2,1,02,6]deca-3,8-diene) in its reaction with cyclopentadiene. The structures of the Diels–Alder adducts were determined by a combination of chemical and spectroscopic methods; the n.m.r. spectra of the adducts are discussed in detail, and a correlation between structure and 19F n.m.r. spectral parameters is presented. No Diels–Alder adducts were obtained when perfluorocyclopentadiene was heated with tetracyanoethylene, tetrafluoroethylene, perfluorobutadiene, perchlorocyclopentadiene, or perchlorobutadiene.Pyrolysis of dimethyl 1,2,3,4,7,7-hexafluoro[2,2,1]hepta-2,5-diene-5,6-dicarboxylate gave dimethyl tetrafluorophthalate and difluorocarbene, which was trapped with cyclohexene. Pyrolysis of perfluoro-(3-methyl-2-oxa-3-azabicyclo[2,2,1]hept-5-ene) was investigated, and its fluorination with cobalt trifluoride gave a compound believed to be perfluoro-(3-methyl-2-oxa-3-azabicyclo[2,2,1]heptane).

10 citations

Journal ArticleDOI
TL;DR: In this article, the ozonization of norbornadiene was described, and the intermediate with silver oxide furnishes 4-cyclopentene-cis-1, 3-dicarboxylic acid.
Abstract: The ozonization of norbornadiene is described. Oxidation of the intermediate with silver oxide furnishes 4-cyclopentene-cis-1, 3-dicarboxylic acid, reduction with sodium borohydride cis-1, 3-bis-hydroxymethylcyclopent-4-ene. The latter was converted to cis-3, 5-dimethylcyclopentene by reduction of the corresponding bis-tosylate with LiAlH4. Hydrogenation of the ozonization intermediate over palladium-lead carbonate (Lindlar's catalyst) afforded 4-cyclopentene-cis-1, 3-dialdehyde. This reaction represents a new and selective method for the reduction of unsaturated ozonization intermediates.

10 citations

Journal ArticleDOI
TL;DR: Pt(CH3)-CF3)(NBD) was found to react with neutral ligands L to give cis-PtCH3-CF3)L2 (L2 = 1,2-bis(diphenylphosphino)ethane (dppe); 2,2′-dipyridyl (bipy); N,N,N′,N-tetramethylethylenediamine (tmen); and L = pyridine (py); dimethylsulfoxide-S (DMSO

10 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202316
202240
202133
202040
201930
201829