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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 12
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Original Articles

A Convenient Synthesis of Theaspirone, An Odoriferous Principle of Black Tea

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Pages 899-904 | Published online: 05 Dec 2006

References

  • Presented in part on the EUCHEM Conference on Structure, Synthesis and Biosynthesis of Mono- and Sesquiterpenoids . august , Varenna, , Italy
  • Ina , K. , Sakato , Y. and Fukami , H. 1968 . Tetrahedron Letters , : 2777
  • Bricout , J. , Viani , R. , Müggler-Chavan , F. J. P. , Reymond , D. Marion and Egli , R. H. 1967 . Helv. Chim. Acta , 50 : 1517
  • Nakatani , Y. and Yamanishi , T. 1969 . Tetrahedron Letters , : 1803
  • Sato , A. and Mishima , H. 1969 . Tetrahedron Letters , : 1803
  • Heckman , R. A. and Roberts , D. L. 1969 . Tetrahedron Letters , : 2701
  • Neth. Patent Appl. . 76. 01551 .
  • Kaiser , R. and Lamparsky , D. 7th International Congress of Essential Oils . October , Kyoto, , Japan Papers published in 1979, p. 395
  • Marx , J. N. 1975 . Tetrahedron , 31 : 1252
  • Könst , W. M. B. and Maessen , J. Th.M.F. in press . Synthetic Communications , A safe method for the preparation of this reagent was not at hand at that moment. However we succeeded in the development of an unique procedure resulting in a safe handling of large quantities of this versatile oxidation reagent. This procedure is described by
  • CHETAH calculations9 reveal that allylic oxidations with DTBC have a very high reaction enthalphy. For α-pinene to verbenone (Yield 50%) −ΔH is about 45–70 Kcal/mole α-pinene, depending on the stoichiometry. It is therefore essential that the oxidizing reagent is added slowly over a certain time to prevent a possible run-away of the reaction

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