2,4-Diorganyl 1,3,2,4-dithiadiphosphetane-2,4-disulfides, their structure and S-silyl dithiophosphonic derivatives

GRAPHICAL ABSTRACT

ABSTRACT

Novel 2,4-diorganyl 1,3,2,4-dithiadiphosphetane-2,4-disulfides were prepared by the reactions of tetraphosphorus decasulfide with butylphenyl ether or 3-brominephenyl-1-isoamyl ether in 1,2-dichlorobenzene. Their structures were established by X-ray single crystal diffraction. Chiral S-trimethylsilyl dithiophosphonates were prepared by the reactions of 2,4-diorganyl 1,3,2,4-dithiadiphosphetane-2,4-disulfides with trimethyl silyl ethers of monoterpenols. Unsaturated S-trimethylsilyl dithiophosphonates were synthesized by the reactions of 2,4-diorganyl 1,3,2,4-dithiadiphosphetane-2,4-disulfides with O-trimethylsilyl ethers of geraniol, nerol, and (R,S)-linalool. S-Esters of dithiophosphonic acids, which possessed antimicrobial activity, were prepared by the reactions of chiral S-trimethylsilyl dithiophosphonates with orthoformiates, acetals and thioacetals.

KEYWORDS:

• 1,3,2,4-Dithiadiphosphetane-2,4-disulfides
• dithiophosphorylation
• monoterpenols
• silylation

Funding

The study was performed with financial support of the Russian Foundation for Basic Researches (Grant No. 14-03-00897-a).