Cyclic Sulfones. The Condensation of Ethyl Oxalate with Arylmethyl Sulfones

Abstract

We have undertaken the preparation of thiophene-l-dioxides in order to study the attack of free radicals on a vinyl sulfone group (-CH= CH-SOz-) contained in a ring. We are also interested in the reactivity of these thiophene-ldioxides as dienes in the Diels-Alder reaction. This paper will describe the condensation of ethyl oxalate with arylmethyl sulfones (R = 0-naphthyl, phenyl, p-chlorophenyl) to give 2,5-diaryl-3,4 -dihydroxythiophene -1 -dioxides (I). The method is outlined below. Na+OET@ R-CHa-SOz--CH~-R

Persulfurated Benzene‐Cored Asterisks with π‐Extended ThioNaphthyl Arms: Synthesis, Structural, Photophysical and Covalent Dynamic Properties

“…Prior to some chemical, photophysical and structural studies on the π-extended thionaphthyl systems ( 5) and ( 6), the preparation of reference persulfurated benzene-cored asterisks (3) [8] and (4) [9] was achieved according to known literature methods. The reference thiomethylated naphthalene regioisomers (1) [23] and (2) [24] were also synthesized (see Supporting Information), according to common procedures for methylating aromatic thiols. Thus, 1-naphthalenethiol reacted with an excess of iodomethane (potential carcinogen!)…”

Recent trends in isomeric thienoquinoxalines [1980‐2000]

“…The treatment of thieno[2,3-b]quinoxaline-2-carbamide 21 with sodium nitrite in acetic acid afforded the corresponding 1,2,3-triazino[4',5':4,5]thieno[2,3-b]quinoxalinone 76, followed by the thiolation using phosphorus pentasulfide and by the chlorination using phosphorus oxychloride to give the corresponding 4-thio and 4-chloro-1,2,3-triazino compounds 77a,b, respectively. Furthermore, hydrazinolysis of the chloride 77b with hydrazine hydrate afforded the 4-hydrazino derivative 78 which was used as a starting material to prepare 1,2,3-triazolo[4",3":1',6'] [1,2,3]triazino [4',5':4,5] thieno[2,3-b]quinoxalines 79a,b [37,38] (Scheme 33).…”

“…The "history of thienoquinoxalines" actually began in 1950 with the synthesis of 1,3-dihydro-1,3-diphenylthieno [3,4-b]quinoxaline-2,2-dioxide by Overberger et al [1]. The fusion of quinoxalines with the thiophene ring was expected to yield seven isomers of thienoquinoxalines, such as thieno [2,3- The literature survey revealed that only three isomers of thienoquinoxalines 1a, 1b, and 3a are known.…”

Zur Reaktion der Alkalimetallsulfide mit Organohalogenverbindungen unter besonderer Berücksichtigung entgiftender Vorgänge

“…Neben Benzylchlorid, das mittels Na}:) in Ausbeuten von 80-90% in Dibenzylsulfid uberfuhrt werden konnte [29], [30], wurden zahlreiche mono-und diphenylsubstituierte Benzylhalogenide in ihrem Reaktionsverhalten untersucht [29], [32], [33], so z. B. das p-Chlor-benzylohlorid.…”