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Title: Synthesis and properties of heterofulvenes. Derivatives of 2,6-dimethyl-.gamma.-pyrone, -.gamma.-thiapyrone, and N-butyl-2,6-dimethyl-.gamma.-pyridone

Abstract

Oxygen-, sulfur-, and nitrogen-containing heterofulvenes, derivatives of 2,6-dimethyl- gamma -pyrone (1) and - gamma -thiapyrone (2) and Nbutyl-2,6- dimethyl- gamma -pyridone (3), have been prepared, and their properties are reported. The 0 and S heterocycles were prepared by condensation of 1 and 2, respectively, with active methylene compounds in acetic anhydride. The N heterocycles were obtained from the 0 heterocycles by reaction with butylamine. Side reactions were observed when butylamine reacted with methyl 2,6dimethyl-4H- pyran-4-ylidenenitroacetate (6) and 2,6-dimethyl4H-pyran-4-ylidenenitroacetone (5). A new convenient route to heterofulvenes which bear a single substituent at the exocyclic double bond was developed. Thus, heterofulvenes substituted by an acetyl group at the exocyclic double bond were found to undergo acetyl cleavage, under very mild acidic conditions, resulting in the formation of monosubstituted heterofulvenes. Deuterium exchange reactions in the systems under consideration were studied. The NMR, UV, and IR data of the disubstituted and monosubstituted heterofulvenes are discussed in terms of the heteroatom and the substituents at the exocyclic double bond.

Authors:
; ;
Publication Date:
Research Org.:
Tel Aviv Univ., Israel
Sponsoring Org.:
USDOE
OSTI Identifier:
4336236
NSA Number:
NSA-29-029094
Resource Type:
Journal Article
Journal Name:
Journal of Organic Chemistry
Additional Journal Information:
Journal Volume: 39; Journal Issue: 7; Other Information: Orig. Receipt Date: 30-JUN-74; Journal ID: ISSN 0022-3263
Country of Publication:
Country unknown/Code not available
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; *DEUTERIUM- ISOTOPIC EXCHANGE; HETEROCYCLIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANIC OXYGEN COMPOUNDS; ORGANIC SULFUR COMPOUNDS; REACTION KINETICS

Citation Formats

Belsky, I., Dodiuk, H., and Shvo, Y. Synthesis and properties of heterofulvenes. Derivatives of 2,6-dimethyl-.gamma.-pyrone, -.gamma.-thiapyrone, and N-butyl-2,6-dimethyl-.gamma.-pyridone. Country unknown/Code not available: N. p., 1974. Web. doi:10.1021/jo00921a028.
Belsky, I., Dodiuk, H., & Shvo, Y. Synthesis and properties of heterofulvenes. Derivatives of 2,6-dimethyl-.gamma.-pyrone, -.gamma.-thiapyrone, and N-butyl-2,6-dimethyl-.gamma.-pyridone. Country unknown/Code not available. https://doi.org/10.1021/jo00921a028
Belsky, I., Dodiuk, H., and Shvo, Y. 1974. "Synthesis and properties of heterofulvenes. Derivatives of 2,6-dimethyl-.gamma.-pyrone, -.gamma.-thiapyrone, and N-butyl-2,6-dimethyl-.gamma.-pyridone". Country unknown/Code not available. https://doi.org/10.1021/jo00921a028.
@article{osti_4336236,
title = {Synthesis and properties of heterofulvenes. Derivatives of 2,6-dimethyl-.gamma.-pyrone, -.gamma.-thiapyrone, and N-butyl-2,6-dimethyl-.gamma.-pyridone},
author = {Belsky, I. and Dodiuk, H. and Shvo, Y.},
abstractNote = {Oxygen-, sulfur-, and nitrogen-containing heterofulvenes, derivatives of 2,6-dimethyl- gamma -pyrone (1) and - gamma -thiapyrone (2) and Nbutyl-2,6- dimethyl- gamma -pyridone (3), have been prepared, and their properties are reported. The 0 and S heterocycles were prepared by condensation of 1 and 2, respectively, with active methylene compounds in acetic anhydride. The N heterocycles were obtained from the 0 heterocycles by reaction with butylamine. Side reactions were observed when butylamine reacted with methyl 2,6dimethyl-4H- pyran-4-ylidenenitroacetate (6) and 2,6-dimethyl4H-pyran-4-ylidenenitroacetone (5). A new convenient route to heterofulvenes which bear a single substituent at the exocyclic double bond was developed. Thus, heterofulvenes substituted by an acetyl group at the exocyclic double bond were found to undergo acetyl cleavage, under very mild acidic conditions, resulting in the formation of monosubstituted heterofulvenes. Deuterium exchange reactions in the systems under consideration were studied. The NMR, UV, and IR data of the disubstituted and monosubstituted heterofulvenes are discussed in terms of the heteroatom and the substituents at the exocyclic double bond.},
doi = {10.1021/jo00921a028},
url = {https://www.osti.gov/biblio/4336236}, journal = {Journal of Organic Chemistry},
issn = {0022-3263},
number = 7,
volume = 39,
place = {Country unknown/Code not available},
year = {Mon Apr 01 00:00:00 EDT 1974},
month = {Mon Apr 01 00:00:00 EDT 1974}
}