1794-96-3Relevant academic research and scientific papers
THE RICH CHEMISTRY OF FULVALENE YLIDES. A DICHOTOMY IN PHOSPHONIUM SALT/YLIDE HYDROLYSIS AND THE DEVELOPMENT OF A NEW SYNTHESIS OF AZULENES
Gilheany, Declan G.,Kelly, Padraig G.,Mitchell, Catherine A.,Walker, Brian J.,Malone, John F.,et al.
, p. 11 - 14 (2007/10/02)
A series of fulvalene ylides was synthesized. Only weak aromatic effects were found across the ylide bond. Their chemistry includes the first example of a dichotomy in phosphonium salt/ylide hydrolysis, interesting dynamic nmrs of the adducts with dimethyl acetylenedicarboxylate and a new synthesis of azulenes.
Structure and stereochemistry of a 7-phosphabicyclohept-2-ene-7-oxide from X-ray, multinuclear NNR, and 2D-J resolved NMR studies
Hocking, Martin B.,Bushnell, Gordon W.
, p. 1020 - 1028 (2007/10/02)
Preparations of a 7-phosphanorbornene, from the reaction of 1,2,5-triphenylphosphole-1-oxide with inhibited acrylonitrile in benzene, were repeated under various conditions to determine if one, or more than one, stereoisomer was formed.Adduct formation fa
PHOSPHORVERBINDUNGEN UNGEWOEHNLICHER KOORDINATION,6. ABFANGVERSUCHE VON PHENYL-THIOXO- UND PHENYL-SELENOXOPHOSPHAN MIT PROTISCHEN NUKLEOPHILEN
Hussong, Rita,Heydt, Heinrich,Regitz, Manfred
, p. 201 - 212 (2007/10/02)
The thioxophosphole 6 undergoes Diels-Alder reaction with the triazolindiones 7a and b to the adducts 8a and b.Analogously 11a and b are formed from the selenoxophosphole 9 and the maleic acid derivatives 10a and b.The triazolindion reactions of 6, 9 and also of 12 suffer considerably under the presence of water.Apart from elemental sulfur and selenium on the one hand phosphole oxides (15) such as secondary products and triazolidindiones (19) on the other hand are formed.Thermolysis of the Diels-Alder adducts 8a and b in toluene proceeds under cycloreversion to 20 and phenyl thioxophosphan (21) which is trapped by alcohols (22,24) under production of phosphinothioates (23,25).Phenyl selenoxophosphane (27) is generated by photochemical decomposition of 11a and b.The trapping reaction with methanol leads to the phosphinoselenoate 29 which is transformed into the phosphonoselenoate 28 under the conditions of the photolysis.
SYNTHESIS AND PHOTOCHEMICAL REACTION OF DIELS-ALDER ADDUCT OF PHOSPHOLE OXIDE AND CYCLOPENTADIENE
Tomioka, Hideo,Miura, Shinichi,Izawa, Yasuji
, p. 3353 - 3356 (2007/10/02)
Irradiation of 1-phenylphosphole oxide-cyclopentadiene adduct gave a caged product, whereas similar irradiation of 1,2,5-triphenylphosphole oxide-cyclopentadiene adduct afforded a cleavaged product.
YLIDE ANALOGUES OF FULVALENES. A STEVENS REARRANGEMENT OF A PHOSPHONIUM YLIDE.
Gilheany, Declan G.,Walker, Brian J.
, p. 183 - 186 (2007/10/02)
Fulvalene-ylides have been synthesised.The pentafulvalene ylide analogue (8) provides the first Stevens rearrangement of a phosphonium ylide and, through reaction with DMAD, a novel 1-phosphabicyclooctratriene ylide.
