Spirocompounds

Spiro compounds presentation. A very old one

1. SPIRO
COMPOUNDS
ORGANIC CHEMISTRY II

2. PLAN
•Definition
•Types
•Nomenclature
•Synthesis
•Chirality
•Uses

3. DEFINITION
A spiro compounds are bi- or
polycyclic organic compounds with
rings connected through just one
atom. The rings can be different in
nature or identical. The connecting
atom is also called the spiroatom,
most often a quaternary carbon
("spiro carbon")

4. TYPES
There’s a mono- (2 rings)
and poly- (3 or more) spiro
compounds
_________________________

5. NOMENCLATURE…
…eight?

6. by Adolf von Baeyer in 1900

PROPOSED

7. MONOSPIRO
COMPOUNDS
All spiro compounds have the
infix spiro followed by square
brackets containing the number
of atoms in the smaller ring and
the number of atoms in the
larger ring excluding the
spiroatom itself; the numbers
being separated by a dot.

8. A is called 1-bromo-3-
chlorospiro[4.5]decan-7-ol and compound
B is called 1-bromo-3-
chlorospiro[3.6]decan-7-ol.

9. POLYSPIRO
COMPOUNDS
When naming polyspiro compounds, the prefixes di-, tri-,
tetra-, etc. are first added to the front of the name to
indicate the amount of spiroatoms, the single atoms
between each ring. The atoms of the compound are
numbered systematically. A polyspiro compound is
numbered starting from a ring that holds one connecting
spiroatom to another ring, i.e. a terminal ring; there can be
two or more terminal rings to a polyspiro compound, so
long as each of these rings has only one connecting
spiroatom. In the terminal ring chosen to start the
numbering, an atom of the ring next, and connected to the
spiroatom, is labeled 1. Each following atom is numbered
one higher than the previous - going around the compound.





dispiro [2.1.3.4] dodecan

10. SYNTHESIS

11. SYNTHESIS
We can obtain spiro compounds
using intramolecular cyclization,
intra/intermolecular condensation

12. SYNTHESIS
Spiro compounds can also be obtained by
regrouping another polycyclics

13. Heterocyclic spiro compounds are
produced by the methods used in
synthesis of simple heterocyclic
compounds
SYNTHESIS

14. CHIRALITY
*term used to describing an object that is
non-superposable on its mirror image
*

15. CHIRALITY
Some spiro
compounds exhibit
axial chirality.
Spiroatoms can be
centers of chirality
even when they lack
the required four
different substituents
normally observed in
chirality.

16. USES
•Spiro compounds used as plasticizers
(eg, glycerinacetal cyclic ketons), in
perfumery, intermediate products in
the synthesis of epoxy, in producing
medicine. some spiro compounds are
used as photochromic materials
•Spiro forms of lactones and oxazines
are frequently used as leuco dyes,
frequently displaying chromism -
reversible change between their
colorless and color form.

18. NURLYBEK
amangeldiuly


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