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Paper | Regular issue | Vol 89, No. 4, 2014, pp.981-993
Published online, 21st February, 2014
DOI: 10.3987/COM-14-12943
Efficient Synthesis of 2-Alkylidene-4H-3,1-benzoxathiin-4-ones and Determination of Their Double Bond Configuration

Masao Shimizu,* Masaki Yamanaka, Wataru Ando, Shigeru Shimada, Takeo Konakahara, and Norio Sakai

*Innovative Oxidation Team, Interdisciplinary Research Center for Catalitic Chemistry, National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan

Abstract

2-Alkylidene-4H-3,1-benzoxathiin-4-ones were efficiently synthesized by reaction of 2-(acylthio)benzoic acids with condensation reagents in the presence of base. The E and Z isomers of the products were distinguished by comparison of the chemical shifts of the vinylic protons in the 1H NMR spectra of the 4H-3,1-benzoxathiin-4-ones and their corresponding 1-oxides.