PAYNE-LIKE REARRANGEMENT OF N-TOSYL-OXIRANEMETHYLAMINES - A NEW ROUTE TO FUNCTIONALIZED AZIRIDINES

The reaction of N-tosyl-oxiranemethylamines with aqueous sodium hydroxide affords N-tosyl-aziridinemethanols in excellent yields, through the intramolecular epoxide ring opening by the nitrogen atom of the tosylamino group.

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Bibliographic Details
Published inTetrahedron letters Vol. 33; no. 4; pp. 487 - 490
Main Authors MOULINES, J, CHARPENTIER, P, BATS, JP, NUHRICH, A, LAMIDEY, AM
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EPOXYNITRILE CYCLIZATION
ACID
PROTECTED ALLYLIC AMINES
RING SIZE
SELENIDES
DERIVATIVES
BETA-LACTAMS
ALLYLAMINES
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Summary:The reaction of N-tosyl-oxiranemethylamines with aqueous sodium hydroxide affords N-tosyl-aziridinemethanols in excellent yields, through the intramolecular epoxide ring opening by the nitrogen atom of the tosylamino group.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)93976-5