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Synthesis and claisen rearrangement of 1-allyloxy-1-carbomethoxy allenes

โœ Scribed by M.J. Sleeman; G.V. Meehan

Book ID
104229393
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
281 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A number of ally1 allenyl ethers (1) have been synthesised and shown to undergo the Claisen rearrangement.

The kinetics of rearrangement of (lb) together with stereochemical data obtained, is consistent with a concerted mechanism for these rearrangements.

A number of variants of the Claisen rearrangement in which the olefinic R systems of ally1 vinyl ether are replaced by other x systems are known. For example, the ally1 group has been replaced by propargyl', benzy12 and alleny13 groups,

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โœ Ernst Egert; Holger Beck; Dieter Schmidt; Charlotte Gonschorrek; Dieter Hoppe ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 262 KB

syn-Allene carbinol la or its esters 11 are transformed to sterically loaded 1,3arkad-I-rcarbamates 6 and 15 by Claisen rearrangement with high stereoselectivity. The structures of 6 and 15a were elucidated by single crystal X-ray analyses.