A CONCISE SYNTHESIS OF THE 2,3-DIMETHYLENE-1,4-METHANO-1,2,3,4-TETRAHYDRONAPHTHALENE AND ITS REACTION WITH SINGLET OXYGEN

被引：12

作者：

ATASOY, B ^{[1
]}

BAYRAMOGLU, F ^{[1
]}

HOKELEK, T ^{[1
]}

机构：

[1] HACETTEPE UNIV,DEPT PHYS BEYTEPE,ANKARA,TURKEY

来源：

TETRAHEDRON | 1994年 / 50卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)85643-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed carbomethoxylation of benzonorbornadiene (7) yielded dimethyl-1,4-methano-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate (9) which was transformed in three steps into 2,3-dimethylene-1,4-methano-1,2,3,4-tetrahydronaphthalene (4) in a high yield. Reaction of 4 with singlet oxygen resulted in the formation of epoxy-endoperoxide (12). X-ray crystallographic analysis demonstrated that epoxide ring is exo as methylene bridge. For the first time, the epoxy-endoperoxide formation from the ''one pot'' reaction of a diene with singlet oxygen was observed. The epoxy-endoperoxide formation mechanism was discussed. CoTPP (Cobalt(II)tetraphenylporphyrin) catalyzed rearrangement of epoxy-endoperoxide gave hydroxy-aldehyde (13) which was oxidized into dialdehyde (14).

引用

页码：5753 / 5764

页数：12

共 28 条

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