𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of [14C6-3,4,7,8,11,12]-(1E,5E,9E)-cyclododeca-1,5,9-triene

✍ Scribed by Bruce N. Diel; Mingcheng Han; Jonathan M. White

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
87 KB
Volume
50
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Trimerization of butadiene in the presence of Ni(0) affords (1__E__,5__E__,9__E__)‐cyclododeca‐1,5,9‐triene 1 (ttt‐CDT), (1__E__,5__E__,9__Z__)‐cyclododeca‐1,5,9‐triene 2 (ttc‐CDT), and other isomers/oligomers. After optimization of reaction conditions, [^14^C~6~‐3,4,7,8,11,12]‐ttt‐CDT 1 was synthesized efficiently either by homogenous or heterogeneous Ni(0) catalytic trimerization of [1,4‐^14^C~2~]butadiene 10, in 60–82% yield. Depending on the exact reaction conditions employed, the yields and ratio of 1/2 ranged from (59–90%) / (41–10%). The all‐trans isomer was conveniently isolated via Ag^+^‐mediated reversed‐phase HPLC. The important intermediate [1,4‐^14^C~2~]‐1,3‐butadiene 10 was prepared from potassium [^14^C]cyanide and 1,2‐dibromoethane 3 as starting materials, in seven steps with a 57% yield. The total radioactive yield of [^14^C~6~‐3,4,7,8,11,12]‐ttt‐CDT 1 is 30% from [^14^C]KCN. Copyright © 2007 John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

Synthesis of 2E, 4E, 8E - nonatetraenoic
Synthesis of 2E, 4E, 8E - nonatetraenoic acid-3, 7-dimethyl-1-[14C]-9-(2′, 6′, 6′-trimethylcyclohex-1-enyl)-4-(N-acetamino) phenylester
✍ Ute J. Haynes; J. E. Swigor 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 French ⚖ 134 KB 👁 1 views

## Abstract The title compound 4‐(N‐acetylamino) phenyl‐1‐[^14^C] retinoate (3) was synthesized by a 2‐step sequence. Carboxyl‐[^14^C] vitamin A (1) was treated with ethylchloroformate to form the mixed anhydride (2). Treatment with acetamidophenol and heating with a catalytical amount of 4‐dimethy

Synthesis of novel 6,7-dihydro-5H-pyrimi
Synthesis of novel 6,7-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-8(9H)-ones
✍ Jinbao Xiang; Xiaowei Hu; Qun Dang; Xu Bai 📂 Article 📅 2011 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 84 KB

## Abstract A new method was developed for the synthesis of 6,7‐dihydro‐5__H__‐pyrimido[4,5‐__e__][1,4]diazepin‐8(9__H__)‐one derivatives. The key to construct the pyrimido[4,5‐__e__][1,4]diazepine core is the intramolecular amidation of __N__‐((4‐amino‐6‐chloropyrimidin‐5‐yl)methyl)‐substituted am