✦ LIBER ✦

Versuche zur basenkatalysierten Bicyclisierung von trans-2-Carbäthoxy-6-dodecen-11-on-säure-äthylester

✍ Scribed by C. A. Grob; R. Moesch

Publisher: John Wiley and Sons
Year: 1959
Tongue: German
Weight: 528 KB
Volume: 42
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19590420313

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✦ Synopsis

Abstract

Attempts to bicyclize ethyl trans‐2‐carbethoxy‐ll‐keto‐6‐dodecenoic acid (I) to the decalol derivative II by an abnormal MICHAEL reaction are described.

Failure of the reaction to occur is attributed to the energetically unfavourable transition state associated with nucleophilic addition of the carbanionic centre in Ia to a non‐conjugated olefinic double bond.

Compound I was prepared by a stepwise synthesis from 4‐pentyne‐1‐01.

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✍ H. Aebli; C. A. Grob 📂 Article 📅 1957 🏛 John Wiley and Sons 🌐 German ⚖ 502 KB

## Abstract Ethyl β‐(2‐oxo‐3‐methyl‐3‐carbethoxy‐6‐cyclohexenyl)‐propionate (I) was synthesized __via__ diethyl α‐methyl‐β‐oxo‐pimelate (Va) and the __Michael__‐addition of diethyl malonate studied.