Abstract
trans-Cyclooctene, cis,trans-1,5-cyclooctadiene, and cis,trans-1,3-cyclooctadiene have been compared with the cis and cis,cis isomers and with 2,5-norbornadiene for competition with ethylene for binding in mung bean sprouts and tobacco and for action (induction of chlorophyll degradation) in banana. The compounds containing a trans double bond were much more effective in competition for binding and action than the cis and cis,cis compounds. trans-Cyclooctene and cis,trans-1,3-cyclooctadiene were in the general range of 50–90 times more effective than 2,5-norbornadiene.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bach RD, and Richter RF (1973) The reactivity of alkenes in the oxymercuration reaction. Tetrahedron Letters 42: 4099–4102
Burg SP and Burg EA (1967) Molecular requirements for the biological activity for ethylene. Plant Physiol 42: 144–152
Chow YL, Buono-Core GE and Shen Y (1984) Photoisomerization of cis,cis-1,5-cyclooctadiene in the presence of copper (I) complexes: Wavelength depencence. Organometallics 3: 702–708
Cope AC and Bumgardner CL (1956) Cyclic polyolefins. XL. cis-cis- and cis-trans-1,3-cyclooctadiene from cyclooctene-3-yldimethylamine. Jour Amer Chem Soc 78: 2812–2815
Hartley FR (1973) Thermodynamic data for olefin and acetylene complexes of transition metals. Chem Rev 73: 163–190
Hines JN, Peagram MJ, Thomas EJ, and Whitham GH (1973) Some reactions of benzaldehyde acetals with alkyl-lithium reagents: A stereospecific olefin synthesis from 1,2-dioles. Jour Chem Soc Perkin I 2332–2337
Hiyama T and Nozaki H (1973) A facile, stereospecific preparation of olefins from pinacols. Bull Chem Soc Jap 46: 2248–2249
Liu RS (1967) Photosensitized isomerization of 1,3-cyclooctadienes and conversion to bicyclo(4.2.0)oct-7-ene. Jour Amer Chem Soc 89: 112–114
Muhs MA and Weiss FT (1962) Determination of equilibrium constants of silver-olefin complexes using gas chromatography. Jour Amer Chem Soc 84: 4697–4705
Rencken I and Orchard SW (1986) Formation constants of copper (I) chloride complexes with cis,cis-1,5-cyclooctadiene and other cyclic olefins. Inorganic Chem 25: 1972–1976
Sisler EC (1977) Ethylene activity of some π-acceptor compounds. Tobacco Sci 21: 43–45
Sisler EC (1979) Measurement of ethylene binding in plant tissue. Plant Physiol 64: 538–542
Sisler EC (1980) Partial purification of an ethylene-binding component from plant tissue. Plant Physiol 66: 404–406
Sisler EC and Blankenship SM (1989) Interaction of trans-cyclooctene and 6,6-dimethylfulvene with the ethylene binding site. Plant Physiol 89: S194
Sisler EC and Pian A (1973) Effect of ethylene and cyclic olefins on tobacco leaves. Tobacco Sci 17: 68–72
Sisler EC and Wood C (1988) Competition of unsaturated compounds with ethylene for binding and action in plants. Plant Growth Reg 7: 181–191
Sisler EC and Yang SF (1984) Anti-ethylene effects of cis-2-butene and cycloolefins. Phytochemistry 23: 2765–2768
Young RE, Pratt HK and Biale JB (1952) Manometric determination of low concentrations of ethylene. Anal Chem: 551–555
Author information
Authors and Affiliations
Additional information
R.J. Reynolds Research Apprentice
Rights and permissions
About this article
Cite this article
Sisler, E.C., Blankenship, S.M. & Guest, M. Competition of cyclooctenes and cyclooctadienes for ethylene binding and activity in plants. Plant Growth Regul 9, 157–164 (1990). https://doi.org/10.1007/BF00027443
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00027443