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The reaction of cyanoguanidine with formaldehyde. I. Hydroxymethylation and methoxymethylation of cyanoguanidine.
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- Takimoto Michiaki
- Department of Chemistry, Faculty of Science, Toho University
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- Ebisuno Toichi
- Department of Chemistry, Faculty of Science, Toho University
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- Shiba Ryuichi
- Department of Applied Science, Faculty of Technology, Tokyo Denki University
Bibliographic Information
- Other Title
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- ChemInform Abstract: THE REACTION OF CYANOGUANIDINE WITH FORMALDEHYDE. I. HYDROXYMETHYLATION AND METHOXYMETHYLATION OF CYANOGUANIDINE
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Description
In order to examine the reactivity of cyanoguanidine (CG) with formaldehyde, CG was first hydroxymethylated, then methoxylated, and finally exhaustively hydroxymethylated with a large excess of formaldehyde. 4-Cyanoimino-3-methoxymethylperhydro-1,3,5-oxadiazine was isolated as a major reaction product of 1,3-bis(methoxymethyl)-2-cyanoguanidine with formaldehyde. This product is an adduct of 3 mol of formaldehyde per mole of CG and a six-membered cyclic ether. Minor products were further methoxylated and 3,5-bis(methoxymethyl)-4-methoxymethyl(carbamoylimino)perhydro-1,3,5-oxadiazine was isolated. This is an adduct of 2 mol of formaldehyde to the amidinated product derived from the major product by the hydration of the cyano group. The ring structure of perhydro-1,3,5-oxadiazine was so stable that it could not be decomposed under acidic conditions if the methoxymethyl groups were fully acid-hydrolyzed.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 56 (11), 3319-3322, 1983
The Chemical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001204124189824
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- NII Article ID
- 130001985766
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- ISSN
- 13480634
- 21992924
- 00092673
- 00092975
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- Text Lang
- en
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- Data Source
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- JaLC
- Crossref
- CiNii Articles
- OpenAIRE
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- Abstract License Flag
- Disallowed