Tropon

Structural formula
General
Surname	Tropon
other names	Tropylium oxide Cycloheptatrienone 2,4,6-cycloheptatrien-1-one
Molecular formula	C 7 H 6 O
External identifiers / databases
CAS number 539-80-0 EC number 208-725-6 ECHA InfoCard 100.007.933 PubChem 10881 Wikidata Q413630
properties
Molar mass	106.12 g mol −1
density	1.094 g cm −3 (25 ° C)
boiling point	113 ° C (20 h Pa )
Refractive index	1.6172 (22 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tropone is a carbocyclic compound . It has a high dipole moment (14.3 · 10 ⁻³⁰ C · m) and extraordinary chemical and spectroscopic properties. Among other things, it does not enter into the reactions typical of ketones . Tropon can also be understood as tropylium oxide (right formula):

The mesomeric stabilized tropylium oxide forms a newly built seven-membered ring with six π electrons, which fulfills the Hückel rule , i.e. is an aromatic .

synthesis

The reaction of bromobenzene with diazomethane in UV light yields bromotropilides which, through bromination and subsequent elimination of hydrogen bromide, yields bromotropylium bromide . Its hydrolysis leads to tropon.

Individual evidence

1. ↑ ^{a b c d} data sheet Tropon at Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).
2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-126.
3. ^ Hans Beyer and Wolfgang Walter: Textbook of Organic Chemistry , S. Hirzel Verlag, Stuttgart 1984, ISBN 3-7776-0406-2 , pp. 616–617.