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Inverse electron-demand 1,3-dipolar cycloaddition reactions of cyclooctyne with pyridinium bis(methoxycarbonyl)methylides

✍ Scribed by Kiyoshi Matsumoto; Naoto Hayashi; Yukio Ikemi; Mitsuo Toda; Takane Uchida; Kinuyo Aoyama; Yoshihiro Miyakoshi

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
55 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Cyclooctyne underwent 1,3‐dipolar cycloaddition with pyridinium bis(methoxy‐carbonyl)methylides to afford the corresponding indolizines (8‐methoxycarbonyl‐7‐azatricyclo[7.6.0.0^2‐7^]pentadeca‐1,3,5,8‐tetraenes) in good to moderate yields. Some molecular orbital considerations are also described on this reaction compared with the results on the reaction of pyridinium dicyanomethylides with cyclooctyne.

📜 SIMILAR VOLUMES

1,3-Dipolar cycloaddition reactions of c
1,3-Dipolar cycloaddition reactions of cyclooctyne with pyridinium dicynomethylides
✍ Kiyoshi Matsumoto; Ryuji Ohta; Takane Uchida; Hiroyasu Nishioka; Maki Yoshida; A 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 387 KB

## Abstract Cyclooctyne smoothly underwent 1,3‐dipolar cycloaddition with pyridinium dicyanomethylides to afford the corresponding indolizines (8‐cyario‐7‐azatricyclo[7.6.0.0^2,7^]pentadeca‐1,3,5,8‐tetraenes) in excellent yields.

Inverse-electron demand [π2 + σ2 + σ2] c
Inverse-electron demand [π2 + σ2 + σ2] cycloaddition reaction of dimethyl oxaquadricyclane-2,3-dicarboxylate with cyclooctyne
✍ Kiyoshi Matsumoto; Hiroyuki Taketsuna; Jong Chul Kim; Akikazu Kakehi 📂 Article 📅 2001 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 66 KB

## Abstract A first example of an inverse‐electron demand [~π~2 + ~σ~2 + ~σ~2] cycloaddition reaction of dimethyl oxaquadricyclane‐2,3‐dicarboxylate was reported: cyclooctyne underwent cycloaddition with dimethyl oxaquadricyclane‐2,3‐dicarboxylate to afford the corresponding adducts one of whose st