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Reaction of singlet oxygen with α,β-unsaturated aldimines

✍ Scribed by Takeshi Akasaka; Kikuko Takeuchi; Wataru Ando


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
266 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis


The reaction of singlet oxygen with N-l-(Z-alkenylidene)-tbutylamines ( 1 and 2 ) gives the unsaturated hemiperacetal derivatives ( 2 and 4 ) of the hydroperoxy aldimines ( 2 and 6 ).

Several a,8-unsaturated aldimines which are held in the s-trans conformation failed to react with singlet oxygen.


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The reactions of a-lithiated saturated aldimines with various electrophiles have been widely utilized to synthesize a variety of organic compounds. l-4) To our knowledge, the alkylation of the metalated a,b-unsaturated aldimines has not been reported. In this communication we wish to report on the r