Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 4
28
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Regioselective Intramolecular Carbon-Hydrogen Insertion in Copper-Catalyzed Carbenoid Decompositions of cis-1-Methyl-3-Arylcyclohexane-1-Diazomethyl Ketones : Some Synthetic Applications

, , &
Pages 275-281 | Received 18 Feb 1975, Published online: 05 Dec 2006
 

Abstract

Recently, we have developed1 a new route for the stereo-specific introduction of an angular carboxyl or functionalized methyl groups2 in a rigid hydrophenanthrene moiety. The key step in this approach is a regioselective intramolecular α-keto carbenoid insertion across the benzylic C-H bond (at C-4a) in CuSO4-catalyzed thermal decomposition of the diazoketones and to the corresponding tetracyclic ketones and in moderate to good yields. A modified procedure3 of carbenoid decomposition of these diazoketones, in the presence of Cu2O under irradiation with tungsten filament lamp, improves the yields of the desired C-H insertion products. Thus, the ketones and have been prepared now in consistently higher yields (53-55%) from the pure diazoketones , m.p. 125-127°, and , m.p.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.