✦ LIBER ✦

Nucleophilic Addition to C, C-Double Bonds. IV. Ether formation by intramolecular addition to unsymmetrically alkyl-substituted C, C-double bonds

✍ Scribed by Gerardo M. Ramos Tombo; Rolland A. Pfund; Camille Ganter

Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 531 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640320

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Tricyclic olefinic alcohols containing an unsymmetrically alkyl‐substituted C, C‐double bond were cyclized intramolecularly to their corresponding ethers under basic conditions: 9 → 12, 10 → 17 + 18, and 11 → 12 (Scheme 3, Table 1). The reactivity is mainly due to relieve of ground state strain.

Alcohol 9 (endocyclic double bond) isomerized under intramolecular assistance by the hydroxyl group to 11 (exocyclic double bond) before cyclization to 12 occurred (Scheme 5). The latter step being the faster one, no isomerization 11 → 9 was observed.

📜 SIMILAR VOLUMES

Nucleophilic addition to C, C-double bon

Nucleophilic addition to C, C-double bonds. VI. Intramolecular addition of primary amines to C, C-double bonds induced by steric compression

✍ Gerardo M. Ramos Tombo; Camille Ganter 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 412 KB 👁 1 views

## Abstract The tricyclic olefinic primary amine **1** readily cyclizes to the tetracyclic secondary amine **2** at approximately 200° in protic as well as aprotic solvents although the C, C‐double bond is not activated by electron‐attracting groups. This unusual intramolecular addition is the cons

Nucleophilic Addition to C, C Double Bon

Nucleophilic Addition to C, C Double Bonds. Proximity and homoconjugative effects. Preliminary communication

✍ Rolland A. Pfund; Camille Ganter 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 German ⚖ 266 KB 👁 1 views

## Abstract Proximity effects alone as well as in combination with electronic effects are responsible for the observed phenomenon of base‐catalyzed ether formation initiated by nucleophilic attack on a C, C double bond of the tricyclic olefin alcohols **1–10** __(Scheme 1, Table 1)__. With compoun

ChemInform Abstract: Cinchona-Catalyzed

ChemInform Abstract: Cinchona-Catalyzed Nucleophilic Conjugate Addition to Electron-deficient C—C Double Bonds

✍ Ji Woong Lee; Hyeong Bin Jang; Choong Eui Song 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 15 KB 👁 1 views

ChemInform Abstract: Cinchona-Catalyzed

ChemInform Abstract: Cinchona-Catalyzed Nucleophilic 1,2-Addition to C—O and C-N Double Bonds

✍ Hyeong Bin Jang; Ji Woong Lee; Choong Eui Song 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 18 KB 👁 2 views

nucleophilic addition to C,C-double bond

nucleophilic addition to C,C-double bonds. VII. Study of proximity effects in olefinic alcohols and amines by photoelectron spectroscopy

✍ Gerardo M. Ramos Tombo; Hans Jakob Ammann; Klaus Müller; Camille Ganter 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 416 KB 👁 2 views

The influence of steric compression on electronic structure in polycyclic olefinic alcohols and amines is studied by PE. spectroscopy. The unsubstituted alcohol **2** and amine **7** show PE.‐spectroscopic properties that can be reconciled by postulating a predominance of intramolecularly H‐bonded

Diastereoselective Additions to C—C Doub

Diastereoselective Additions to C—C Double Bonds Applied to the Enantioselective Synthesis of Pyrethroic Acids

✍ Alain Krief; Alexandre Froidbise 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 8 KB 👁 1 views