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preface to fifteenth edition

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1.12 SECTION 1<br />

TABLE 1.4<br />

Suffixes for Specialist Nomenclature of Heterocyclic Systems<br />

Number of<br />

ring<br />

Rings containing nitrogen Rings containing no nitrogen<br />

members Unsaturation* Saturation Unsaturation* Saturation<br />

3<br />

4<br />

5<br />

6<br />

7<br />

8<br />

9<br />

10<br />

-irine<br />

-ete<br />

-ole<br />

-ine†<br />

-epine<br />

-ocine<br />

-onine<br />

-ecine<br />

-iridine<br />

-etidine<br />

-olidine<br />

‡<br />

‡<br />

‡<br />

‡<br />

‡<br />

-irene<br />

-ete<br />

-ole<br />

-in<br />

-epin<br />

-ocin<br />

-onin<br />

-ecin<br />

-irane<br />

-etane<br />

-olane<br />

-ane§<br />

-epane<br />

-ocane<br />

-onane<br />

-ecane<br />

* Unsaturation corresponding <strong>to</strong> the maximum number of noncumulative double bonds. Heteroa<strong>to</strong>ms have<br />

the normal valences given in Table 1.3.<br />

† For phosphorus, arsenic, antimony, and boron, see the special provisions in Table 1.3.<br />

‡ Expressed by prefixing perhydro- <strong>to</strong> the name of the corresponding unsaturated compound.<br />

§ Not applicable <strong>to</strong> silicon, germanium, tin, and lead; perhydro- is prefixed <strong>to</strong> the name of the corresponding<br />

unsaturated compound.<br />

If the corresponding carbocyclic system is partially or completely hydrogenated, the additional<br />

hydrogen is cited using the appropriate H- or hydro- prefixes. A trivial name from Tables 1.5 and<br />

1.6, if available, along with the state of hydrogenation may be used. In the specialist nomenclature<br />

for heterocyclic systems, the prefix or prefixes from Table 1.3 are combined with the appropriate<br />

stem from Table 1.4, eliding an a where necessary. Examples of acceptable usage, including (1)<br />

replacement and (2) specialist nomenclature, are<br />

(1) 1-Oxa-4-azacyclohexane<br />

(2) 1,4-Oxazoline<br />

Morpholine<br />

(1) 1,3-Diazacyclohex-5-ene<br />

(2) 1,2,3,4-Tetrahydro-1,3-diazine<br />

(1) Thiacyclopropane<br />

(2) Thiirane<br />

Ethylene sulfide<br />

Radicals derived from heterocyclic compounds by removal of hydrogen from a ring are named<br />

by adding -yl <strong>to</strong> the names of the parent compounds (with elision of the final e, if present). These<br />

exceptions are retained:<br />

Furyl (from furan)<br />

Pyridyl (from pyridine)<br />

Piperidyl (from piperidine)<br />

Quinolyl (from quinoline)<br />

Isoquinolyl<br />

Thenylidene (for thienylmethylene)<br />

Furfuryl (for 2-furylmethyl)<br />

Furfurylidene (for 2-furylmethylene)<br />

Thienyl (from thiophene)<br />

Thenylidyne (for thienylmethylidyne)<br />

Furfurylidyne (for 2-furylmethylidyne)<br />

Thenyl (for thienylmethyl)<br />

Also, piperidino- and morpholino- are preferred <strong>to</strong> 1-piperidyl- and 4-morpholinyl-, respectively.

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