2738. Cyclooctyne

Nomenclature

CAS number: 1781-78-8
C8H12; mol wt 108.18.
C 88.82%, H 11.18%.

Description and references

Highly strained, highly reactive cycloalkyne. Prepn: A. T. Blomquist, L. H. Liu, J. Am. Chem. Soc. 75, 2153 (1953); G. Wittig, A. Krebs, Ber. 94, 3260 (1961). Improved synthesis: L. Brandsma, H. D. Verkruijsse, Synthesis 1978, 290. Molecular structure: M. Traetteberg et al., J. Mol. Struct. 128, 217 (1985). Review of synthetic applications: D. Heber et al., Eur. J. Org. Chem. 2005, 4231-4247.

Chemical structure

Properties

bp740 157.5-158°. bp20 50-55°. mp -34° to-32°. nD20 1.4876. d420 0.868.

Use

Building block in cycloaddition reactions.