Reactions of thebaine derivatives with trifluoroacetyl acetylenes: [4+2]-addition solely
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- 作者：Irina V. Sandulenko ; Daria V. Semenova ; Maria V. Zelentsova ; Sergey K. Moiseev ; skm@ineos.ac.ru" class="auth_mail" title="E-mail the corresponding author ; Andrey B. Koldobskii ; Alexandr S. Peregudov ; Ivan S. Bushmarinov ; Valery N. Kalinin
- 关键词：Trifluoroacetyl acetylenes ; Thebaine ; Diels-Alder cycloaddition ; Azocines
- 刊名：Journal of Fluorine Chemistry
- 出版年：2016
- 出版时间：September 2016
- 年：2016
- 卷：189
- 期：Complete
- 页码：7-12
- 全文大小：466 K
文摘
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Trifluoroacetyl acetylenes produce [4+2]-adducts solely with thebaine derivatives.
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N-Acyl derivatives of thebaine must be used to produce the [4+2]-adducts.
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The trifluoroacetyl substituted [4+2]-adducts easily rearrange to benzazocines.
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The rearrangement can be prevented by the addition of a nucleophile.
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Thebaine itself reacts with trifluoroacetyl acetylenes via a nucleophilic pathway.