Issue 8, 1989
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Addition-rearrangement reactions of N-(arylsulphonyloxy)amines and 3,4-dihydro-2H-pyran

Robert V. Hoffman  and  James M. Salvador  

Abstract

A series of N-alkyl-O-(arylsulphonyl)hydroxylamines (NSA) was treated with 3,4-dihydro-2H-pyran (DHP). Acid-catalysed addition to the double bond followed by cationic rearrangement gave cyclic imidates from hydride migration (major) and ring expansion (minor), which were reduced to amino alcohols for analysis. The results indicate that NSA function as nucleophiles which capture the oxonium ion produced by protonation of DHP, and give new NSA derivatives that rearrange to the observed products.

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Article information

DOI
https://doi.org/10.1039/P19890001375
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 1375-1380

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Addition-rearrangement reactions of N-(arylsulphonyloxy)amines and 3,4-dihydro-2H-pyran

R. V. Hoffman and J. M. Salvador, J. Chem. Soc., Perkin Trans. 1, 1989, 1375 DOI: 10.1039/P19890001375

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