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Spirocompounds
- 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. TYPESThere’s a mono- (2 rings) and poly- (3 or more) spiro compounds _________________________
- 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 COMPOUNDSWhen 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. CHIRALITYSome 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.