C-Nitroso compounds. Part XXXVI. Rearrangement of 2-chloro-2-nitrosofenchane and 2-chloro-2-nitrosocamphane.

J. Lub, Th.J. de Boer

Research output: Contribution to journalArticleAcademicpeer-review

13 Citations (Scopus)

Abstract

2-Chloro-2-nitrosofenchane (I, R = Me, R1 = H) rearranged in the presence of AlCl3 to give the chloro nitrones II (R = Me, R1 = H) and III, whereas 2-chloro-2-nitrosocamphane (I, R = H, R1 = Me) under similar conditions gave only II (R = H, R1 = Me). II and III reacted with common nucleophiles and were easily reduced to the amides IV [X, X1, R, R1 = CO, NH, H, Me (V); CO, NH, Me, H; NH, CO, Me, H (VI)]. V and VI are not accessible by Beckmann rearrangement of the appropriate oxime.
Original languageEnglish
Pages (from-to)328-332
Number of pages5
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume103
Issue number11
DOIs
Publication statusPublished - 1984
Externally publishedYes

Bibliographical note

M1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.

CAPLUS AN 1985:95835(Journal)

Keywords

  • rearrangement chloronitrosofenchane chloronitrosocamphane
  • azabicyclooctanone trimethyl
  • fenchane chloronitroso rearrangement
  • camphane chloronitroso rearrangement

Fingerprint Dive into the research topics of 'C-Nitroso compounds. Part XXXVI. Rearrangement of 2-chloro-2-nitrosofenchane and 2-chloro-2-nitrosocamphane.'. Together they form a unique fingerprint.

Cite this