The Preparation of Optically Pure 7‐Oxabicyclo [2.2.1]hept‐2‐ene Derivatives. The CD Spectrum of (+)‐(1<i>R</i>)‐7‐Oxabicyclo [2.2.1]hept‐5‐en‐2‐one
書誌事項
- 公開日
- 1983-09-21
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/hlca.19830660627
- 公開者
- Wiley
この論文をさがす
説明
<jats:title>Abstract</jats:title><jats:p>(−)‐1‐Camphanoyloxyacrylonitrile (=(−)‐1‐cyanovinyl camphanate; <jats:bold>1</jats:bold>) obtained from the commercially available (−)‐camphanoyl chloride and 2‐oxo‐propiononitrile added to furan at 20° in the presence of Cu (BF<jats:sub>4</jats:sub>)<jats:sub>2</jats:sub> · 6H<jats:sub>2</jats:sub>O or ZnI<jats:sub>2</jats:sub> and gave a mixture of 2‐cyano‐7‐oxabicyclo [2.2.1]hept‐5‐en‐2‐yl camphanates (<jats:bold>2–5</jats:bold>) from which isomer <jats:bold>5</jats:bold> could be obtained pure by crystallization. The latter was transformed into (+)‐(1<jats:italic>R</jats:italic>)‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐one (<jats:bold>6</jats:bold>) in high yield and optical purity. Adducts <jats:bold>2–4</jats:bold> were recycled into <jats:bold>1</jats:bold>+furan by heating in toluene, and (−)‐camphanic acid was recovered after saponification of <jats:bold>5</jats:bold>. The absolute configuration of <jats:bold>6</jats:bold> was deduced from its <jats:bold>CD</jats:bold> spectrum which showed two 1200‐cm<jats:sub>−1</jats:sub> <jats:italic>Franck</jats:italic>‐<jats:italic>Condon</jats:italic> series for its n→π<jats:inline-graphic xmlns:xlink="http://www.w3.org/1999/xlink" xlink:href="graphic/tex2gif-stack-1.gif" xlink:title="urn:x-wiley:0018019X:media:HLCA19830660627:tex2gif-stack-1"/> transition.</jats:p>
収録刊行物
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- Helvetica Chimica Acta
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Helvetica Chimica Acta 66 (6), 1865-1871, 1983-09-21
Wiley
