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

J. Lub; Th.J. de Boer

doi:10.1002/recl.19841031106

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 journal › Article › Academic › peer-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 language	English
Pages (from-to)	328-332
Number of pages	5
Journal	Recueil des Travaux Chimiques des Pays-Bas
Volume	103
Issue number	11
DOIs	https://doi.org/10.1002/recl.19841031106
Publication status	Published - 1984
Externally published	Yes

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

Access to Document

10.1002/recl.19841031106

Cite this

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title = "C-Nitroso compounds. Part XXXVI. Rearrangement of 2-chloro-2-nitrosofenchane and 2-chloro-2-nitrosocamphane.",

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.",

keywords = "rearrangement chloronitrosofenchane chloronitrosocamphane, azabicyclooctanone trimethyl, fenchane chloronitroso rearrangement, camphane chloronitroso rearrangement",

author = "J. Lub and {de Boer}, Th.J.",

year = "1984",

doi = "10.1002/recl.19841031106",

language = "English",

volume = "103",

pages = "328--332",

journal = "Recueil des Travaux Chimiques des Pays-Bas",

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

number = "11",

}

TY - JOUR

T1 - C-Nitroso compounds. Part XXXVI. Rearrangement of 2-chloro-2-nitrosofenchane and 2-chloro-2-nitrosocamphane.

AU - Lub, J.

AU - de Boer, Th.J.

PY - 1984

Y1 - 1984

N2 - 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.

AB - 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.

KW - rearrangement chloronitrosofenchane chloronitrosocamphane

KW - azabicyclooctanone trimethyl

KW - fenchane chloronitroso rearrangement

KW - camphane chloronitroso rearrangement

U2 - 10.1002/recl.19841031106

DO - 10.1002/recl.19841031106

M3 - Article

SN - 0165-0513

VL - 103

SP - 328

EP - 332

JO - Recueil des Travaux Chimiques des Pays-Bas

JF - Recueil des Travaux Chimiques des Pays-Bas

IS - 11