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New Innovative Methods for IUPAC Nomenclature of Bicyclo and Spiro

Compounds in Organic Chemistry

Article  in  Indian Journal of Applied Research · October 2011

DOI: 10.15373/2249555X/JULY2013/189

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 Research Paper Science Volume : 3 | Issue : 7 | July 2013 | ISSN - 2249-555X

New Innovative Methods for IUPAC Nomenclature

of Bicyclo and Spiro Compounds in Organic
Chemistry

Keywords Fused ring system, Bicyclo, Spiro, Common points (CP), Big, Small.

DR ARIJIT DAS
HEAD, Department of Chemistry, Govt. Degree College, Dharmanagar, Tripura(N), Tripura, India.
ABSTRACT IUPAC nomenclature of bicyclo and spiro compounds is a vitally important to students of organic chemistry
in graduate and also in post-graduate level. This new innovative method has to be introduced for informal
determination of IUPAC nomenclature of bicyclo and spiro compounds in a very simple way, which is also be a time savings
one.

Bicyclo[4,1,0]heptane {Here the maximum no of points, ‘a’

INTRODUCTION
The method which is generally used for determination of
IUPAC nomenclature of bicyclo and spiro compounds1,2,3 is
time consuming. To keep the matter in mind a new innova-
tive method has to be introduced for determination of IUPAC
naming of bicyclo and spiro compounds in a very simple way,
which is also be a time savings one. Another two innovative
methods also to be introduced earlier on the easy predic-
tion of ‘Hybridization’ and ‘Bond-Order’ 4,5 for the benefit of
students.
= 4, are denoted by asterisk mark, minimum no of points,
‘b’=1, are denoted by positive sign and common points, cp
= 2, are denoted by shadow circle.}
In case of substituted bicyclo compounds numbering is to
be started from the one bridgehead and is continued to the
next longest bridge and thus the shortest bridge is num-
bered later on.
Non substituted bicyclo compounds:

New Innovative Rules For Nomenclature of Bicyclo Com-

pounds bicyclo[2,1,0]pentane bicyclo[3,1,0]hexane bicyclo[3,2,0]heptane bicyclo[2,2,0]hexane
Compounds containing two fused rings are named as bicy-
clo compounds. Incase of bicyclo compounds the common
points of two fused rings are at least 02 (two). It may be
more than two i.e. it may be three, four etc. but not less than
bicyclo[4,1,0]heptane bicyclo[2,2,1]heptane bicyclo[2,2,2]octane bicyclo[4,4,0]decane
two. The common points (cp), may also be treated as car-
bons, which are common in two fused rings.
Substituted bicyclo Compounds:-

2 1
The format of writing of IUPAC nomenclature for non sub- 3 1 9
2
1
8
stituted bicyclo compounds is ‘bicyclo[a,b,c]alkane’ and 4 3
6 5 4 2
6 3
for substituted bicyclo compounds are ‘x-substituent 5 7 4
8-methylbicyclo[4,3,0]nonene 6-methylbicyclo[2,1,1]hexane 1,2,3,4-tetramethylbicyclo[1,1,0]butane
bicyclo[a,b,c]alkane’ (in presence of only one substitu-
1
ent); ‘x-substituent name bicyclo[a,b,c]alkene/alk-y-ene’ 2 6
(in presence of one double bond and one substituent) ; 3 5
‘x,x-disubstituent name bicyclo[a,b,c]alkene/alk-y-ene’ (in 4

presence of one double bond and two same substituents) 1,4-dimethylbicyclo[3,1,0]hex-2-ene.

and ‘x,x-disubstituent name bicyclo[a,b,c]alka-y,z-diene’
(in presence of two double bonds and two same substitu-
ents). Here ‘a’ and ‘b’ are the maximum and minimum num-
ber of points respectively in the fused ring system excluding
common points and variable ‘c’ = no of common points (cp)
– 2; x = position no of the substituents present in the ring sys-
tem; y and z = position numbers of the double bonds and the
suffix ‘alkane’ corresponding to the total number of points/
carbons in the fused ring system including common points.
Since in ‘bicyclo’, ‘b’ stands for ‘big’ i.e. supreme (maxi-
mum), so, during IUPAC naming first we write in the third
parenthesis ‘[ ]’, maximum no of points followed by minimum
(least) no of points and then write variable number ‘c’ al-
ways accomplish by the deduction of 02 (two) from the total
number of common points [i.e. variable c = no of common
points (cp) – 2]. Sometimes, where a = b, then write ‘a’ after
‘b’ or vice versa.
New Innovative Rules For Nomenclature of Spiro Com-
pounds:-
In Spiro compounds two rings are passing through only one
point elected as common point. In such case, common
point (cp) is always one.
The format of writing of IUPAC nomenclature for non sub-
stituted spiro compounds is ‘spiro[a,b]alkane’ and for
substituted spiro compounds are ‘x-substituent name
spiro[a,b]alkane’ (in presence of only one substituent); ‘x-
substituent name spiro[a,b]alkene/alk-y-ene’ (in presence
of one double bond and one substituent) ; ‘x,x-disubstit-
uent name spiro[a,b]alkene/alk-y-ene’ (in presence of one
double bond and two same substituents) and ‘x,x-disub-
stituent name spiro[a,b]alka-y,z-diene’ (in presence of two
double bonds and two same substituents). Here ‘a’ and
‘b’ are the minimum and maximum number of points respec-
tively in the fused ring system excluding common point (cp);
x = position no of the substituents present in the ring system;
y and z = position numbers of the double bonds and the suf-
fix ‘alkane’ corresponding to the total number of points i.e.
carbon atoms in the ring system including common point.

Since in ‘spiro’, ‘s’ stands for ‘small’ i.e. minimum , so, dur-

596 X INDIAN JOURNAL OF APPLIED RESEARCH

 Research Paper Volume : 3 | Issue : 7 | July 2013 | ISSN - 2249-555X

ing IUPAC naming of spiro compounds first write in the third CONCLUSIONS:
parenthesis ‘[ ]’, minimum no of points ‘a’ followed by maxi- This article is very helpful to students in chemistry of gradu-
mum no of points ‘b’ . Sometimes, where a = b, then write ate and also in Postgraduate level. This is one of the very
‘a’ after ‘b’ or vice versa. time savings method. By using this method student can pre-
dict bond order in a very simple way.
In case of numbering of substituted spiro compounds al-
ways give priority to the smaller ring system and the num- ACKNOWLEDGEMENT:
bering starts from the atom next to the common point (cp) Author would be grateful to Prof. R.N.Mukherjee, Direc-
and proceeds to the smaller ring first and bigger ring later tor, IISER, Kolkata; Prof.G.N.Mukherjee, Sir Rashbehary
on. Ghose Professor of Chemistry, Calcutta University, India,;
Prof.A.K.Das, Ex Vice-Chancellor of Kalyani University,
Prof.R.A.Lal, Head, Dept. of Chemistry, NEHU, Shillong,
cp=1
Prof. Md.Ali, Dept. of Chemistry, Jadavpur University,
7 1
6 Prof. R.K.Nath, Head, Deptt. of Chemistry, Tripura Central
a=2
b=4 University for their recognition in this regard.
3
5 4 2

Spiro[2,4]heptane
{Here the minimum no of points, ‘a’ = 2, and maximum no of
points, ‘b’=4, are denoted by arrow mark and the common
point, cp = 1, are denoted by asterisk mark .}

Non Substituted Spiro compounds:-

Spiro[2,5]octane Spiro[2,4]heptane Spiro[4,5]decane

Substituted Spiro compounds:-

7 8 1 7 1 9 10 1
6 6 2
3 5 3 8 5 3
5 4 2 4 2
7 6 4
6-methylspiro[2,5]oct-4-ene Spiro[2,4]hept-5-ene 8,8-dimethylspiro[4,5]deca-1,6-diene

REFERENCE 1. I.L.Finar, Organic Chemistry, Vol-1, 6th Ed (Pearson), p532. | 2. R.T. Morrison, R.N.Boyd and S.K.Bhattacharjee, Organic Chemistry, 7th Ed (Pearson),
p208. | 3. T.W.Graham Solomons and C.B.Fryhle, Organic Chemistry, 10th Ed (Wiley India), 2012, p150. | 3. Arijit Das, ‘Indian Journal of Applied Re-
search’, July 2013 (in press). | 4. Arijit Das, ‘Indian Journal of Applied Research’, July 2013 (in press).

INDIAN JOURNAL OF APPLIED RESEARCH X 597

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