80016-35-9Relevant academic research and scientific papers
Dioxopyrrolines. XXXVI. Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Acyclic Olefins. Structural and Stereochemical Assigment of the Photocycloadducts
Sano, Takehiro,Horiguchi, Yoshie,Tsuda, Yoshisuke,Furuhata, Kimio,Takayanagi, Hiroaki,Ogura, Haruo
, p. 9 - 22 (2007/10/02)
The photocycloaddition of the dioxopyrroline 1 to olefins with electron donating substituents proceeded with regio- and stereo-selectivity to give the 7-substituted 2-azabicycloheptane-3,4-diones 2 and 3, together with, in a few instances, the dihydropyridone 4.The stereochemistries of the adducts were dependent on the nature of the olefins.Olefins carrying phenyl, vinyl, and alkyl substituents afforded the exo-adducts 2, while olefins carrying an O-substituent afforded the endo-adducts 3, predominantly.The structures of these cycloadducts were established by X-ray crystallographic analyses, chemical correlations, and spectroscopic means.Keywords-photocycloaddition; 1H-pyrrole-2,3-dione; dioxopyrroline; 2-azabicyclo-heptane-3,4-dione; electron rich olefin; stereochemistry; cycloadduct; X-ray analysis
2-Azabicycloheptane-3,4-diones (5). Stereodependency in thermal rearrangement of 7-vinyl-2-azabicycloheptane-3,4-diones and their imidates
Sano, Takehiro,Horiguchi, Yoshie,Kambe, Suetaka,Toda, Jun,Taga, Jun-ichi,Tsuda, Yoshisuke
, p. 893 - 896 (2007/10/02)
The thermal reaction of the 7-vinyl-2-azabicycloheptane-3,4-dione yielded different products depending on the stereochemistry of 7-vinyl group.The endo isomer, either the lactam (3) or the imidates (8) afforded a Cope product (5 or 9) (3,3-sigmatro
2-AZABICYCLOHEPTANE-3,4-DIONES (2): STEREOCHEMISTRY OF THE PHOTO-CYCLOADDUCTS OF 3-ETHOXYCARBONYL-2-PHENYL-Δ2-PYRROLINE-4,5-DIONE WITH SUBSTITUTED OLEFINS.
Sano, Takehiro,Horiguchi, Yoshie,Tsuda, Yoshisuke
, p. 359 - 362 (2007/10/02)
The stereochemistries of photo-cycloadducts of 3-ethoxycarbonyl-2-phenyl-Δ2-pyrroline-4,5-dione with substituted olefins were established by chemical and spectroscopic means.Styrene- and butadiene-major adducts were 7-exo-isomers, while ethyl vinyl ether- and vinyl acetate-major adducts were 7-endo-isomers.The 7,7'-disubstitutsd derivative, the isopropenyl acetate-adduct, was also established as an O-endo-isomer.
