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The thermal rearrangement of diethyl α-methylallyl and diethyl crotyl phosphites

✍ Scribed by Anthony L. Lemper; Howard Tieckelmann

Book ID
104240707
Publisher
Elsevier Science
Year
1964
Tongue
French
Weight
322 KB
Volume
5
Category
Article
ISSN
0040-4039

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✦ Synopsis

Rearrangements of diethyl a-methylallyl phosphite (I) and diethyl crotyl phosphite (II) have recently been reported by Pudovik and Aladshyeva (1,2) to give only the products resulting from inversion of the migrating allylic groups. They accounted for the products by an intramolecular rearrangement (2) similar to the Claisen rearrangement (3): ': CH* 7" (C2H50)2P\o,CH-~' R AH / 'CH > (C2H5G)2R*, :H-R' while we have observed that the rearrangement of the a-methyl-ally1 phosphite I gave only diethyl crotylphosphonate (III), rearrangement of the crotyl phosphite II gave the crotylphosphonate III in addition to the previously reported product

(2) diethyl a-methylallylphosphonate (IV).

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