140934-66-3Relevant articles and documents
Reaction of Aromatic N-Oxides with Dipolarophiles. Part 18. Formation Mechanism and X-Ray Structure of the Cycloadduct from Sequential Pericyclic Reaction of Pyridine N-Oxides with Phenylsulfonylallene.
Matsuoka, Toshikazu,Hasegawa, Tomoaki,Eto, Masashi,Harano, Kazunobu,Hisano, Takuzo
, p. 1859 - 1866 (2007/10/02)
Sequential pericyclic reactions of pyridine N-oxides (1) with phenylsulfonylpropadiene (2) and 1-phenylsulfonylpropyne (3) were investigated. 3,5-Dimethylpyridine N-oxide (1a) was allowed to react with 2 in CHCl3 at room temperature to give a mixture of the -sigmatropic rearrangement product (4a) of the 1:1 cycloadduct and the 1:2 azetidine-type cycloadduct (5a).The structure of 5a was established by single crystal X-ray analysis.The reaction rate of 1a with 2 was about 50000 times that of 1a with N-phenylmaleimide.The reactionof 1a with 3 did not give 5a but 4a as the sole product.The reactivity, regio- and peri-selectivity and formation mechanism of 4 and 5 are discussed in terms of the frontier molecular orbital consideration based on kinetic and molecular orbital calculation data.
REACTION OF AROMATIC N-OXIDES WITH DIPOLAROPHILES. XVII. CYCLOADDITION BEHAVIOUR OF ALLENES TOWARD PYRIDINE N-OXIDES AND FORMATION OF AZETIDINE-TYPE CYCLOADDUCT
Matsuoka, Toshikazu,Hasegawa, Tomoaki,Harano, Kazunobu,Hisano, Takuzo
, p. 179 - 188 (2007/10/02)
3,5-Dimethylpyridine N-oxide was allowed to react with phenylsulfonylpropadiene in CHCl3 at room temperature to give a mixture of the 1:1 sigmatropic rearrangement product and the 1:2 azetidine-type cycloadduct.The structure of the azetidine-type cy
