Tetrahedron letters

Spin selectivity in the oxygenation of singlet phenylhalocarbenes with oxygen

T Makihara, T Nojima, K Ishiguro, Y Sawaki

Index: Makihara, Taiki; Nojima, Takayuki; Ishiguro, Katsuya; Sawaki, Yasuhiko Tetrahedron Letters, 2003 , vol. 44, # 4 p. 865 - 868

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Citation Number: 9

Abstract

Singlet phenylhalocarbenes are shown to react with triplet oxygen and the apparent spin- forbidden oxygenation rates are strongly dependent on substituents, ie in the decreasing order of Br> Cl≫ F for halogen and of p-NO2> H≫ p-MeO for p-substituents. These results suggest the oxygenation of triplet halocarbene equilibrated with ground-state singlet, resulting in the first estimation of energy difference between the singlet and triplet states.

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