𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Ring expansion of isopropenyldihydrofuran derivatives

✍ Scribed by Seiji Yamaguchi; Nao Tsuchida; Kayoko Umeda; Hajime Yokoyama; Masahiro Miyazawa; Yoshiro Hirai

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
358 KB
Volume
43
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

Lactonization of 2‐(hydroxymethyl)‐5‐isopropenyl‐4,5‐dihydrofuran‐3‐carboxylic acids 1a,b,c with dicyclohexylcarbodiimide gave the corresponding furano‐lactones, 5‐isopropenyl‐5,6‐dihydro‐1(3__H__)‐furo[3,4‐b]furanone 2a,b,c, which were readily converted to the corresponding oxepino‐lactones, 6‐methyl‐5,8‐dihydro‐1(3__H__)‐furo[3,4‐b]oxepinone 3a,b,c by respective thermal ring expansions.

📜 SIMILAR VOLUMES

Isopropenyldihydrofuran derivatives. Pre
Isopropenyldihydrofuran derivatives. Preparation and reactions of some isopropenyldihydrofurandicarboxylates
✍ Seiji Yamaguchi; Yosbihiko Sugioka; Miwa Ishida; Hajime Yokoyama; Yoshiro Hirai 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 538 KB

## Abstract Diethyl 5‐isopropenyl‐4,5‐dihydrofuran‐2,3‐dicarboxylate 1a and methyl 5‐isopropenyl‐3‐methoxy‐carbonyl‐4,5‐dihydrofuran‐2‐acetate 2a were prepared by cylization of diethyl 2‐oxosuccinate or dimethyl 3‐oxoglutarate with (__E__)‐1,4‐dibromo‐2‐methyl‐2‐butene. Their chemical properties we