preface to fifteenth edition

1.32 SECTION 1
hydroxyamino- to the parent name. For example, C 6 H 5 NHOH would benamed N-phenylhydroxylamine,
but HOC 6 H 4 NHOH would be(hydroxyamino)phenol, with thepoint of attachment indicated
by a locant preceding the parentheses.
Compounds of thetypeR 1 NH9OR 2 are named (1) as alkoxyamino derivatives of compound
R 1 H, (2) as N,O-substituted hydroxylamines, (3) as alkoxyamines (even if R 1 is hydrogen), or
(4) by the prefix aminooxy- when another substituent has priority for parent name. Examples of
each type are
1. 2-(Methoxyamino)-8-naphthalenecarboxylic acid for CH 3 ONH9C 10 H 6 COOH
2. O-Phenylhydroxylamine for H 2 N9O9C 6 H 5 or N-phenylhydroxylamine for C 6 H 5 NH9OH
3. Phenoxyamine for H 2 N9O9C 6 H 5 (not preferred to O-phenylhydroxylamine)
4. Ethyl (aminooxy)acetate for H 2 N9O9CH 2 CO9OC 2 H 5
Acyl derivatives, RCO9NH9OH and H 2 N9O9CO9R, arenamed as N-hydroxy derivatives
of amides and as O-acylhydroxylamines, respectively. The former may also be named as
hydroxamic acids. Examples are N-hydroxyacetamide for CH 3 CO9NH9OH and O-acetylhydroxylaminefor
H 2 N9O9CO9CH 3 . Further substituents are denoted by prefixes with O- and/or N-
locants. For example, C 6 H 5 NH9O9C 2 H 5 would be O-ethyl-N-phenylhydroxylamine or N-ethoxylaniline.
For oximes, the word oxime is placed after the name of the aldehyde or ketone. If the carbonyl
group is not theprincipal group, usetheprefix hydroxyimino-. Compounds with thegroup N9OR
are named by a prefix alkyloxyimino- as oxime O-ethers or as O-substituted oximes. Compounds
with thegroup C"N(O)R arenamed by adding N-oxideafter thenameof thealkylideneaminc
compound. For amineoxides, add theword oxide after thenameof thebase, with locants. For
example, C 5 H 5 N9O is named pyridine N-oxideor pyridine1-oxide.
1.1.3.16Imines. Thegroup C"NH is named either by the suffix -imine or by citing the
nameof thebivalent radical R 1 R 2 C as a prefix to amine. For example, CH 3 CH 2 CH 2 CH"NH
could be named 1-butanimine or butylideneamine. When the nitrogen is substituted, as in
CH 2 "N9CH 2 CH 3 , thenameis N-(methylidene)ethylamine.
Quinones are exceptions. When one or more atoms of quinonoid oxygen have been replaced by
NH or NR, they arenamed by using thenameof thequinonefollowed by theword imine (and
preceded by proper affixes). Substituents on the nitrogen atom are named as prefixes. Examples are
p-Benzoquinone monoimine
p-Benzoquinone diimine
1.1.3.17 Ketenes. Derivatives of the compound ketene, CH 2 "C"O, arenamed by substitutive
nomenclature. For example, C 4 H 9 CH"C"O is butyl ketene. An acyl derivative, such as
CH 3 CH 2 9CO9CH 2 CH"C"O, may be named as a polyketone, 1-hexene-1,4-dione. Bisketene
is used for two to avoid ambiguity with diketene (dimeric ketene).
1.1.3.18 Ketones. Acyclic ketones are named (1) by adding the suffix -one to the name of the
hydrocarbon forming theprincipal chain or (2) by citing thenames of theradicals R 1 and R 2 followed