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Substituierte 9-Oxabicyclo[4.2.1]- und 9-Oxabicyclo[3.3.1]nonane III. neue ergiebige synthese von 2, 7-dioxatwistan und endo-2-hydroxy-9-oxabicyclo[3.3.1]nonen- by C. Ganter; W. Zwahlen is a Chemistry article available to read on EtoBox.
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## Abstract Iodine cleavage of the [3.3.1]‐iodomercuri compound **4**, easily prepared from __cis__, __cis__‐cyclooctadiene‐(1,5) by oxymercuration of the monoepoxide **1** (→ **3**) followed by treatment with potassium iodide, leads to three isomeric iodides **6, 7**, and **8**, the [3.3.1]‐__exo__‐iodo isomer 8 being the predominant product. Intramolecular substitution in **8** opens an attractive new route to unsubstituted 2,7‐dioxatwistane (**19**) [2], whereas dehydrohalogenation of **7** and **8** yields the unsaturated alcohol **17** [2], a suitable starting material for the preparation of substituted 2,7‐dioxatwistanes [2], 2,7‐dioxaisotwistanes (**e**) [2], and 2,8‐dioxa‐homotwistbrendanes (**f**).
Who reads Substituierte 9-Oxabicyclo[4.2.1]- und 9-Oxabicyclo[3.3.1]nonane III. neue ergiebige synthese von 2, 7-dioxatwistan und endo-2-hydroxy-9-oxabicyclo[3.3.1]nonen-?
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- Author
- C. Ganter; W. Zwahlen
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)
- Published
- 1971
- Language
- DE
- Field
- Chemistry (Physical Sciences)