Cycloheptatriene

Source: Wikipedia, the free encyclopedia.
Cycloheptatriene
Names
Preferred IUPAC name
Cyclohepta-1,3,5-triene[1]
Other names
1,3,5-Cycloheptatriene
1H-[7]Annulene
CHT
Tropilidene
Identifiers
3D model (
JSmol
)
506066
ChEBI
ChemSpider
ECHA InfoCard
 100.008.061 Edit this at Wikidata
EC Number
  • 208-866-3
1943
UNII
UN number 2603
  • InChI=1S/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2 checkY
    Key: CHVJITGCYZJHLR-UHFFFAOYSA-N checkY
  • InChI=1/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2
    Key: CHVJITGCYZJHLR-UHFFFAOYAI
SMILES
  • C1=C\C/C=C\C=C1
Properties
C7H8
Molar mass 92.141 g·mol−1
Appearance Colourless liquid
Density 0.888 g/mL at 25 °C
Melting point −80 °C (−112 °F; 193 K)
Boiling point 116 °C (241 °F; 389 K)
Insoluble in water
Acidity (pKa) 36
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H225, H301, H304, H311, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P322, P330, P331, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cycloheptatriene (CHT) is an

oxidation
.

Synthesis

Albert Ladenburg first generated cycloheptatriene in 1881 by the decomposition of tropine.[2][3] The structure was finally proven by the synthesis of Richard Willstätter in 1901. This synthesis started from cycloheptanone and established the seven membered ring structure of the compound.[4]

Cycloheptatriene can be obtained in the laboratory by

ring expansion to give 1,3,5-cycloheptatriene 7-carboxylic acid ethyl ester.[6][7]

The Buchner ring expansion, a classical synthesis for cycloheptatriene derivatives
  • Selected cycloheptatriene derivatives
  • Heptalene – composed of two fused cycloheptatriene rings.
    Heptalene – composed of two fused cycloheptatriene rings.
  • Azulene – composed of fused cyclopentadiene and cycloheptatriene rings.
    Azulene – composed of fused cyclopentadiene and cycloheptatriene rings.
  • Sesquifulvalene – composed of linked cyclopentadiene and cycloheptatriene rings.
    Sesquifulvalene – composed of linked cyclopentadiene and cycloheptatriene rings.
  • Elassovalene – composed of one cycloheptatriene and two fused cyclopentene rings.
    Elassovalene – composed of one cycloheptatriene and two fused cyclopentene rings.
  • Tropone – composed of cycloheptatriene ring and carbonyl group.
    Tropone – composed of cycloheptatriene ring and carbonyl group.
  • Tropolone – composed of cycloheptatriene ring, carbonyl and hydroxy groups.
    Tropolone – composed of cycloheptatriene ring, carbonyl and hydroxy groups.
  • Hinokitiol – composed of cycloheptatriene ring, isopropyl, carbonyl and hydroxy groups (isopropyl cycloheptatrienolone).
    isopropyl
    cycloheptatrienolone).

Reactions

Removal of a

tropylium ion. A practical route to this cation employs PCl5 as the oxidant.[8] CHT behaves as a diene in Diels–Alder reactions, for example with maleic anhydride:[9]

Many

metal complexes
of cycloheptatriene are known, including Cr(CO)3(C7H8) [10] and cycloheptatrienemolybdenum tricarbonyl.[11]

Structure of Mo(C7H8)(CO)3.

triplet quencher for rhodamine 6G dye lasers.[12][13]

See also

References

  1. ISBN 978-0-85404-182-4
    .
  2. doi:10.1002/jlac.18832170107
    .
  3. doi:10.1002/cber.188101402127
    .
  4. doi:10.1002/jlac.19013170206
    .
  5. doi:10.1021/jo01084a635
    .
  6. ^ Buchner, et al., Ber., 18, 2377 (1885);
  7. doi:10.1021/ja01325a054
    .
  8. doi:10.15227/orgsyn.043.0101
    .
  9. doi:10.1246/bcsj.44.2993
    .
  10. ^ James H. Rigby, Kevin R. Fales (2004). "7α-ACETOXY-(1Hβ, 6Hβ)-BICYCLO[4.4.1]UNDECA-2,4,8-TRIENE VIA CHROMIUM-MEDIATED HIGHER ORDER CYCLOADDITION". Organic Syntheses; Collected Volumes, vol. 10, p. 1.
  11. doi:10.1021/cr00034a006
    .
  12. doi:10.1039/ft9949000963
    .
  13. doi:10.1063/1.1653190
    .
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