Etude des reactions pericycliques sous pression—IV

Jenner, G.; Rimmelin, J.; Libs, S.; Antoni, F.

doi:10.1016/0040-4020(76)85033-8

Cited by 12 publications

(4 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The aldehyde proved unstable to purification and was carried on as crude material in later experiments. The spectral data for this compound were consistent with the literature data …”

Section: Methodssupporting

confidence: 88%

Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

Jung

Kiankarimi

1998

J. Org. Chem.

View full text Add to dashboard Cite

The series of furyl enone esters, 4a−c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels−Alder reactions to give the tricyclic ketones 5a−c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.

show abstract

“…The aldehyde proved unstable to purification and was carried on as crude material in later experiments. The spectral data for this compound were consistent with the literature data …”

Section: Methodssupporting

confidence: 88%

Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

Jung

Kiankarimi

1998

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Thus, efficient catalytic hydroarylation reactions of olefins such as methyl methacrylate, styrene, or acrylonitrile are not possible due to radical polymerization side reactions. Attempted hydrophenylation of methylvinyl ketone resulted in a previously reported thermal cyclodimerization reaction …”

Section: Resultsmentioning

confidence: 99%

Experimental and Computational Studies of Ruthenium(II)-Catalyzed Addition of Arene C−H Bonds to Olefins

et al. 2004

View full text Add to dashboard Cite

Hydroarylation reactions of olefins are catalyzed by the octahedral Ru(II) complex TpRu-(CO)(NCMe)(Ph) (1) (Tp ) hydridotris(pyrazolyl)borate). Experimental studies and density functional theory calculations support a reaction pathway that involves initial acetonitrile/ olefin ligand exchange and subsequent olefin insertion into the ruthenium-phenyl bond. Metal-mediated C-H activation of arene to form a Ru-aryl bond with release of alkyl arene completes the proposed catalytic cycle. The cyclopentadienyl complex CpRu(PPh 3 ) 2 (Ph) produces ethylbenzene and styrene from a benzene/ethylene solution at 90 °C; however, the transformation is not catalytic. A benzene solution of (PCP)Ru(CO)(Ph) (PCP ) 2,6-(CH 2 P t -Bu 2 ) 2 C 6 H 3 ) and ethylene at 90 °C produces styrene in 12% yield without observation of ethylbenzene. Computational studies (DFT) suggest that the C-H activation step does not proceed through the formation of a Ru(IV) oxidative addition intermediate but rather occurs by a concerted pathway.

show abstract

“…Systematic conditions suggested the space group C 2/ c (Table ). The structure was solved by Direct Methods . The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F 2 .…”

Section: Methodsmentioning

confidence: 99%

Dehydrogenative Route to Metallo Dithiolenes: The Reaction of Zinc Polysulfides and Alkenes

1999

View full text Add to dashboard Cite

Complexes of the type ZnS6(TMEDA), ZnS4(PMDETA), and ZnS4(Me3TACN) react with electrophilic alkenes to give dithiolene complexes ZnS2C2R2(amine) n . The Me3TACN complex is the most reactive, while the more conveniently prepared PMDETA complex also undergoes this reaction at useful rates. The following alkenes were successfully tested: C2H2(CO2Me)2 (cis and trans isomers), C2H3(CO2Me), C2H3(CN), 1,2-C2H2Me(CN), C2H3(CHO), and 1,2-C2H2(CN)(Ph). Crystallographic analysis shows that the highly reactive complex ZnS4(Me3TACN) is structurally similar to ZnS4(PMDETA), including the presence of an elongated Zn−Nax bond. Model studies indicate that the reaction of alkenes with L n ZnS x proceeds via the reversible formation of a dipolar intermediate, as indicated by the ability of the polysulfido complexes to catalyze the isomerization of cis-C2H2(CO2Me)2. It is proposed that such dipolar species undergoes ring closure to give alkanedithiolato intermediates, e.g., Zn[S2C2H2(CO2Me)2](PMDETA). The dithiolato complexes Zn[S2C2H2(CO2Me)2](PMDETA) and Zn[S2C2H2(CO2Me)2](TMEDA) were prepared from ZnMe2, the di- and triamines, and the dithiol meso-(HS)2C2H2(CO2Me)2. These dithiolates undergoes dehydrogenation upon treatment with S8 to give the dithiolene Zn[S2C2(CO2Me)2]L n at a rate that is independent of the ancillary ligand L. The dithiolene ligands can be removed from the Zn center by treatment with [COCl2]3 and Cp2TiCl2; in this way Zn[S2C2H(CN)](PMDETA) was converted to OCS2C2H(CN) and Cp2TiS2C2H(CN).

show abstract

Etude des reactions pericycliques sous pression—IV

Cited by 12 publications

References 16 publications

Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

Experimental and Computational Studies of Ruthenium(II)-Catalyzed Addition of Arene C−H Bonds to Olefins

Dehydrogenative Route to Metallo Dithiolenes: The Reaction of Zinc Polysulfides and Alkenes

Contact Info

Product

Resources

About