Dervan, Peter B. and Santilli, Donald S. (1980) Synthesis and thermal decomposition of cis-3,4,5,6-tetrahydropyridazine-3,4-d2. Relative rates of rotation, cleavage, and closure for tetramethylene. Journal of the American Chemical Society, 102 (11). pp. 3863-3870. ISSN 0002-7863. doi:10.1021/ja00531a031. https://resolver.caltech.edu/CaltechAUTHORS:20160516-092246816
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Abstract
The stereospecific syntheses of cis-3,4,5,6-tetrahydropyridazine-3,4-d₂ (6 ) and cis- and trans-cyclobutane-l,2-d₂ are reported. The thermal decomposition of cis-3,4,5,6-tetrahydropyridazine-3,4-d₂ (6 ) (gas phase, 439°C affords 67.1 ± 0.9% cis-ethylene-1,2-d₂, 16.1 ± 0.8% trans-ethylene-1,2-d₂,9.4 ± 0.4% cis-cyclobutane-1,2-dz, and 7.4 f 0.4% trans-cyclobutane-1.2-d₂. The relative rates of rotation, cleavage, and closure for this 1,2-diazene generated tetramethylene-d₂ are k(cleavage)/k(closure) = 2.2 ± 0.2 and k(rotation)/k(closure) = 12 ± 3. An extra stereospecific cleavage component (46%) superimposed on the 1,4-biradical pathway (54%) from the parent tetrahydropyridazine was found, similar to that observed in the 3,4-dimethyl-3,4,5,6-tetrahydropyridazinthe ermal reactions. Finally, the experimental data for the parent 1.4 biradical, tetramethylene, are compared to calculated values in the literature.
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| Additional Information: | © 1980 American Chemical Society. Received October 22, 1979 Publication Date: May 1980. The authors are grateful to the National Science Foundation (CHE-75-06776) for generous support. | |||||||||
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| Issue or Number: | 11 | |||||||||
| DOI: | 10.1021/ja00531a031 | |||||||||
| Record Number: | CaltechAUTHORS:20160516-092246816 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20160516-092246816 | |||||||||
| Official Citation: | Synthesis and thermal decomposition of cis-3,4,5,6-tetrahydropyridazine-3,4-d2. Relative rates of rotation, cleavage, and closure for tetramethylene Peter B. Dervan and Donald S. Santilli Journal of the American Chemical Society 1980 102 (11), 3863-3870 DOI: 10.1021/ja00531a031 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 67101 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Victoria Brennan | |||||||||
| Deposited On: | 16 May 2016 19:39 | |||||||||
| Last Modified: | 11 Nov 2021 00:27 |
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