This document outlines the nomenclature rules for naming spiro compounds. It discusses: 1) Numbering spiro compounds starting with the smaller ring at the atom adjacent to the spiro atom. 2) Indicating heteroatoms and unsaturation with prefixes and endings. 3) Naming unbranched polyspiro hydrocarbons using prefixes like dispiro- or trispiro- followed by a von Baeyer descriptor in brackets indicating the carbon atoms between spiro atoms, with locants for each spiro atom visited twice. The compound is numbered according to the von Baeyer descriptor order.

1. 1. Nomenclature of Spiro compounds
Monospiro hydrocarbons with two monocyclic rings are numbered consecutively
starting in the smaller ring at an atom next to the spiro atom, proceeding around
the smaller ring back to the spiro atom and then round the second ring.
Example:
spiro[4.5]decane
not spiro[5.4]decane

2. 2. Heteroatoms are indicated by replacement prefixes and unsaturation is
indicated in the usual way by the endings ene, diene, etc.
8-azaspiro[4.5]dec-2-ene
Examples:
spiro[4.4]nona-2,7-diene 3,9-diazaspiro[5.5]undecane
1-bromo-3-chlorospiro[3.6]decan-7-ol

3. 3. Unbranched polyspiro hydrocarbons composed of only monocyclic rings are named
using dispiro-, trispiro-, etc. indicating the total number of spiro atoms present and the
name of the parent hydrocarbon corresponding to the total number of carbon atoms
present. Between the prefix and hydrocarbon name there is placed the von Baeyer
descriptor which indicates the number of carbon atoms linked to the spiro atom or
linking spiro atoms. The numbers are cited in order starting with a terminal ring and
proceeding to the other terminal ring and back to the first via the other linking units.
The numbers are separated by full stops and placed in square brackets.
The compound is numbered in the order in which the numbers of its von Baeyer
descriptor are cited. For trispiro and higher spiro systems each time a spiro atom is
reached for the second time its locant is cited as a superscript number to
the corresponding number of linking atoms.

4. Examples:
dispiro[4.2.4.2]tetradecane trispiro[2.2.2.29.26.23]pentadecane
Note: In previous rules superscript numbers were not used but with the
extension of this system to branched spiro systems where superscript
numbers are essential it is clearer to use them for all polyspiro systems
with three or more spiro atoms using a von Baeyer descriptor.

5. 4. If there is a choice of number the name that gives the lower locants for spiro atoms
is selected.
Example:
dispiro[4.1.5.2]tetradecane
not dispiro[5.1.4.2]tetradecane
not dispiro[4.2.5.1]tetradecane
not dispiro[5.2.4.1]tetradecane
(5,7 is lower than 6,8 or 5,8 or 6,9)

6. 5. If there is still a choice of numbering the numbers of the von Baeyer descriptor
are considered in the order of citation. The name is selected with lower numbers
at the first point of difference.
Example:
trispiro[2.2.2.29.26.33]hexadecane
not trispiro[2.2.2.29.36.23]hexadecane
(2.2.2.29.26.33 is lower than 2.2.2.29.36.23)

7. 6. Branched polyspiro hydrocarbons composed of only monocyclic rings are named
using trispiro-, tetraspiro-, etc. indicating the total number of spiro atoms present
and the name of the parent hydrocarbon corresponding to the total number of
carbon atoms present. Between the prefix and hydrocarbon name there is placed
the von Baeyer descriptor which indicates the number of carbon atoms linked to
the spiro atom or linking spiro atoms. The numbers are cited in order starting
with a terminal ring and proceeding to the next terminal ring and so on to the first
spiro atom. The numbers are separated by full stops and placed in square
brackets. The compound is numbered in the order in which its von Baeyer
descriptor is cited. Each time a spiro atom is reached for the second time its
locant is cited as a superscript number to the corresponding number of linking
atoms.

8. Examples:
•
trispiro[2.2.26.2.211.23]pentadecane
• Note: Without the superscript numbers
this name would be the same as
the name of the second example
without superscript numbers.

9. 7. If there is a choice of numbering the name which gives the lowest locants
for spiro atoms is selected.
Examples:
trispiro[2.0.24.1.28.13]undecane
not trispiro[2.1.25.0.28.13]undecane
not trispiro[2.1.25.1.29.03]undecane
(3,4,8 is lower than 3,5,8 or 3,5,9)

10. tetraspiro[2.2.2.29.2.214.26.23]icosane
not tetraspiro[2.2.2.29.26.2.216.23]icosane
nor tetraspiro[2.2.26.2.2.214.211.23]icosane
(3,6,9,14 is lower than 3,6,9,16 or 3,6,11,14)

11. 8. If there is still a choice of numbering the numbers of the von Baeyer descriptor
are considered in the order of citation. The name is select with lower numbers
at the first point of difference.
Example:
pentaspiro[2.0.24.1.1.210.0.213.18.23]octadecane
not pentaspiro[2.0.24.1.1.210.0.213.28.1sup>3]octadecane
(2.0.24.1.1.210.0.213.18.23 is lower than 2.0.24.1.1.210.0.213.28.1<sup3< sup="">)</sup3<>

12. decaspiro[4.1.0.1.510.28.2.1.0.2.426.223.0.2.436.233.222.120.17.35]nonatetracontane
name decaspiro[4.1.0(1.5).2)2.1.0(2.4).2)0.2.4).2.2.1.1.3]nonatetracontane
Let’s wrap up by briefly covering “spiro” fused compounds. Since both
“bridgehead” positions are on the same carbon, we won’t be able to use the same
“bicyclo” nomenclature as before- but the process is very similar. We simply
substitute “spiro” for “bicyclo”, insert the two bridge lengths, and place the suffix as
before. So, the molecule below is spiro[5.4]decane. Included next door are two
other examples of spiro compounds, spiro[4.3]octane and spiro[5.2]octane.

13. Best Regards