ISSN:
0570-0833
Keywords:
Cyclopropylcarbonyl compounds
;
Cyclization
;
Insertion
;
Dehalogenation
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
There are three important direct routes to cyclopropylcarbonyl compounds: 1. Cyclization of chains of three carbon atoms, the first or third of which is adjacent to a carbonyl or potential carbonyl carbon atom (this type includes syntheses by intramolecular alkylation of γ-halogeno ketones or related compounds in alkaline media); 2. insertion of a methylene group or substituted methylene group into the olefinic double bond of an α,β-unsaturated carbonyl compound; and 3. introduction of an acetonyl group into the double bond of an olefin. However, cyclopropylcarbonyl compounds can also be obtained from 1,2-epoxycyclobutane and 2-bromocyclobutanone derivatives by ring contraction. Another possibility is the dehalogenation of α,α-bis(bromomethyl) cycloalkanones. This review concludes with a discussion of these little known routes and of a particularly suitable method which involves the reaction of methylene iodide, a Zn—Cu couple, and α,β-unsaturated ketones.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.196805701
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