Related Experiment Video
Updated: Jun 1, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(1E,2E)-1,2-Bis(2,3,4-trimeth-oxy-benzyl-idene)hydrazine
Summary
A novel compound, C(20)H(24)N(2)O(6), was unexpectedly synthesized from hydrazinium dithio-carbazate and 2,3,4-trimeth-oxy-benzaldehyde. Its crystal structure reveals a center of inversion and stabilization via weak intermolecular interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Chemical Synthesis
Background:
- Hydrazinium dithio-carbazate is a versatile reagent in organic synthesis.
- 2,3,4-trimeth-oxy-benzaldehyde is an aromatic aldehyde with potential applications.
- Understanding unexpected reaction products aids in developing novel synthetic pathways.
Purpose of the Study:
- To characterize the unexpected product formed from the reaction of hydrazinium dithio-carbazate and 2,3,4-trimeth-oxy-benzaldehyde.
- To elucidate the crystal structure and intermolecular interactions of the synthesized compound.
Main Methods:
- Chemical synthesis involving refluxing ethanol.
- Single-crystal X-ray diffraction analysis.
- Analysis of molecular symmetry and crystal packing.
Main Results:
- The title compound, C(20)H(24)N(2)O(6), was isolated as an unexpected product.
- The molecule crystallizes with a center of inversion.
- Crystal packing is stabilized by weak intermolecular C-H⋯O interactions.
Conclusions:
- The reaction between hydrazinium dithio-carbazate and 2,3,4-trimeth-oxy-benzaldehyde yields an unexpected C(20)H(24)N(2)O(6) compound.
- The structural analysis provides insights into the solid-state behavior of this novel molecule.
- The study highlights the importance of investigating unexpected outcomes in chemical reactions.
Related Concept Videos
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
03:00Preparation of Epoxides
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
02:41Formation of Halohydrin from Alkenes
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
02:38Structure and Nomenclature of Epoxides
Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
02:43E1 Reaction: Stereochemistry and Regiochemistry
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.