Cycloheptatriene (CHT) is an organic compound with the formula C7H8. It is a closed ring of seven carbon atoms joined by three double bonds (as the name implies) and four single bonds. This colourless liquid has been of recurring theoretical interest in organic chemistry. It is a ligand in organometallic chemistry and a building block in organic synthesis. Cycloheptatriene is not aromatic, as reflected by the nonplanarity of the methylene bridge (-CH2-) with respect to the other atoms; however the related tropylium cation is.
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]
^For a variation: Irvin Smith Lee; Tawney Pliny O (1934). "Studies on the Polymethylbenzenes. IX. Addition of Ethyl Diazoacetate to Durene". J. Am. Chem. Soc.56 (10): 2167–2169. doi:10.1021/ja01325a054.
^Green, Malcolm L. H.; Ng, Dennis K. P. (1995). "Cycloheptatriene and -enyl Complexes of the Early Transition Metals". Chemical Reviews. 95 (2): 439–473. doi:10.1021/cr00034a006.
^Tomi Nath Das; K. Indira Priyadarsini (1994). "Triplet of Cyclooctatetraene : Reactivity and Properties". Journal of the Chemical Society, Faraday Transactions. 90 (7): 963–968. doi:10.1039/ft9949000963.