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Synthesis and thermal decomposition of cis-3,4,5,6-tetrahydropyridazine-3,4-d2. Relative rates of rotation, cleavage, and closure for tetramethylene

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00531a031DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00531a031PublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
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.
Funders:
Funding AgencyGrant Number
NSFCHE-75-06776
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Crellin Laboratory of Chemistry6097
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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