Transannular course in the addition of halogen to <i>cis</i>‐cyclo‐octene and in some related reactions

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書誌事項

公開日
1966-01
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/recl.19660851115
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>In reactions of (<jats:italic>cis</jats:italic>)cyclo‐octene with lead tetrachloride and hydrogen chloride/methylene chloride as well as with <jats:italic>N</jats:italic>‐chlorourea and acetic acid/water, transannular reactions were found to prevail. The dichlorocyclo‐octane fractions isolated from the products of the two reactions, both consisted of a mixture of <jats:italic>cis</jats:italic>‐ and <jats:italic>trans</jats:italic>‐1,4‐dichlorocyclo‐octanes, <jats:italic>trans</jats:italic>‐1,2‐dichlorocyclo‐octane and possibly very small amounts of other compounds. The main product of the reaction with <jats:italic>N</jats:italic>‐chlorourea in an acetic acid/water medium under standard conditions (<jats:italic>vide infra</jats:italic>) is 4‐chlorocyclo‐octanol (one isomer), which on treatment with phosphorus pentachloride yields a mixture of the 1,4‐dichlorocyclo‐octanes and some <jats:italic>trans</jats:italic>‐1,2‐dichlorocyclo‐octane. 4‐Chlorocyclo‐octene on addition of hydrogen chloride yields a mixture of <jats:italic>cis</jats:italic>‐ and <jats:italic>trans</jats:italic>‐1,4‐dichlorocyclo‐octanes.</jats:p><jats:p>The reactions leading to the corresponding bromo compounds proceed in a similar way; it proved difficult to perform a controlled reaction with lead tetrabromide, however. With the reaction of bromine and cyclo‐octene “transannular addition” is observed at low temperatures (∼ −100°).</jats:p>

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