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A novel photocycloaddition of allylic silanes to 2,3-dicyano-5,6-dimethylpyrazine: Formation of 2,8-diazatricyclo[3.2.1.04,8]oct-2-ene derivatives

✍ Scribed by Gen-ichi Konishi; Kazuhiko Chiyonobu; Akira Sugimoto; Kazuhiko Mizuno


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
114 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


Irradiation of a benzene solution containing 2,3-dicyano-5,6-dimethylpyrazine with allylic silanes afforded 2,8-diazatricyclo[3.2.1.04.S]oct-2-ene derivatives in moderate yields. This photoreaction involves the (2n + 2n) photecycloaddition followed by rearrangement.


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## Abstract Trichloro‐substituted 8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐ones **6** and **7** are solvolysed by methanolic sodium methoxide to form the bicyclo[3.2.1] Ξ±,α‐dimethoxy ketones **13** and **14**, with preservation of one chloro substituent. In the case of **6a**, prolonged reaction time with an