142506-66-9Relevant articles and documents
SYNTHESIS AND HYDROLYTIC STABILITY OF SOME NEW PHOSPHONODITHIOITE, PHOSPHONODITHIOATE, AND PHOSPHONOTRITHIOATE ESTERS
Kim, Sangha,Mimikakis, John L.,Roundhill, D. Max
, p. 119 - 128 (2007/10/02)
The compounds RP(SCH2CH2CO2CH2CH3)2 (R = (CH3)3C, C6H5) have been prepared from RPCl2 and HSCH2CH2CO2CH2CH3 and base.The compounds react with hydrogen peroxide and with sulfur to give RP(O)(SCH2CH2CO2CH2CH3)2 and RP(S)(SCH2CH2CO2CH2CH3)2 respectively.The 5-membered ring compound has been synthesized from C6H5PCl2 and diethyl 2,3-dimercaptosuccinate and base.The compounds reacts with hydrogen peroxide and with sulfur to give and respectively.Reacting C6H5PCl2 with one equivalent of HSCH2CH2CO2CH2CH3 and base gives C6H5PCl(SCH2CH2CO2CH2CH3), which undergoes hydrolysis to give C6H5PH(O)(SCH2CH2CO2CH2CH3).Except for and C6H5PH(O)(SCH2CH2CO2CH2CH3), the compounds do not undergo significant hydrolytic cleavage of the P-S bond.The hydrolysis of likely proceeds via C6H5PH(O)(SCH(CO2CH2CH3)CH(CO2CH2CH3)SH).The increased hydrolysis rate of C6H5PH(O)(SCH2CH2CO2CH2CH3) is possibly due to hydrogen bonding between water and the PH(O) functionality. Key words: Phosphonodithioite; phosphonodithioate; phosphonotrithioate; hydrogen bonding; NMR spectra.
