Bakkas, Salem published the artcileReactivity of triethyl phosphite with tetrachloromethane: electron transfer versus ionic substitution on positive halogen, SDS of cas: 866-23-9, the publication is Tetrahedron (1987), 43(3), 501-12, database is CAplus.
The mechanism of the reaction of P(OEt)3 (I) with CCl4 (II) was studied. I reacts at 80° with II to form mostly (EtO)2P(O)CCl3 and EtCl. Trichloromethyl radical is trapped by BHT. The reaction is initiated by UV light (254 nm) and a charge-transfer complex is formed between I and II, and the reaction is inhibited by TCNQ. Tris(cyclopropylmethyl) phosphite and tri(1-hexene-6-yl) phosphite are used as potential radical clocks in these reactions. The first leads to CH2:CHCHClMe and the second to CH2:CHCH2CH2CHClMe. The first suggests a radical mechanism (but also may be rationalized by an ionic mechanism), but not the second. Electrochem. oxidation of I with added CCl4 does not account for a radical chain process as the main pathway. Marcus anal. of the reaction viewed as an electron transfer gives a calculated rate constant in the range of 10-20 M-1s-1. Thus, the thermal reaction is in fact an SNCl+ substitution. The radical intermediates are derived from the electron-transfer reaction between CCl3– and CCl4. The reaction of I with II is an example where the observed paramagnetic species during a donor (D)/acceptor (A) interaction suggests an electron-transfer between D and A where in fact they originate from an interaction between A and an electron donor formed after or during the first step of the reaction.
Tetrahedron published new progress about 866-23-9. 866-23-9 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyltrichloromethylphosphonate, and the molecular formula is C5H10Cl3O3P, SDS of cas: 866-23-9.
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https://en.wikipedia.org/wiki/Chloride,
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