Res. Chem. Intermed.
, Vol. 27, No. 6, pp. 659–668 (2001)
Spin trapping with phosphonothionesters. Part VI.
Phosphoryl- and thiophosphoryl-thionformates
, M. BENAGLIA
, A. HUDSON
, D. MACCIANTELLI
and S. MASSON
ICoCEA, Area della Ricerca del CNR, Via P. Gobetti 101, I-40129 Bologna, Italy
Laboratoire de Chimie Moléculaire et Thio-Organique (UMR 6507), ISMRA, 6 Bd Maréchal Juin,
F-1450 Caen, France
Received 7 December 2000; accepted 21 January 2001
Abstract—Ethyl (diethoxyphosphoryl)thionformate, ethyl (diethoxythiophosphoryl) thionformate,
ethyl (diethoxyphosphoryl)thiolformate, and ethyl (diethoxythiophosphoryl)thiolformate have been
allowed to react with a variety of
generated free radicals. Spin adducts were observed by EPR
with the two thionesters but not with thiolesters; even the former compounds, however, exhibited a
remarkably lower reactivity than similarly substituted dithioesters.
Since the emergence of the spin trapping technique in the late sixties , there
has been an ongoing search for new and ef cient spin trapping agents. However,
although a large number of molecules capable of readily undergoing homolytic
addition to give relatively persistent spin adducts have been investigated, 2-methyl-
-phenylnitrone (PBN) and 5,5-dimethyl-
-oxide (DMPO) are by far the most popular compounds
used in spin trapping experiments . Indeed these compounds react with virtually
all radical species, trapping nucleophilic , electrophilic [4 –6], as well as
organometallic species . More recently, 5-diethoxyphosphoryl-5-methyl-4,5-
-oxide, DEPMPO, has joined the list of successful spin traps ,
For previous parts see Ref. .
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