Synthesis p. 390 - 394 (1993)
Update date:2022-08-05
Topics:
Hideg
Sar
Hankovszky
Tamas
Jerkovich
Several 3,4-disubstituted 2,5-dihydro-1H-pyrrol-1-yloxyl radicals were synthesized. 2,5-Dihydro-3-hydroxymethyl-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxyl radical (1) was reacted with triethyl orthoacetate in a Claisen rearrangement to give the exoolefinic compound 2. This was converted to its 1-acetoxyl derivate 3, which was then brominated in the allylic position. Subsequent rearrangement gave the endoolefinic compound 1-acetoxyl-4-bromomethyl-3-ethoxy-carbonylmethyl-2,2,5,5-tetramethyl- 1H-pyrrole radical (4). The allylic bromine could be replaced with nucleophiles (NaSCN, KSeCN, thiourea, selenourea, NaN3 and KSSO2Me) to give 5a-e and 26. The diamagnetic thiocyanates and selenocyanates could be reduced with sodium borohydride to the free thiol and selenol monoradicals, which were oxidized to reversible, ester-functionalized disulfide or diselenide diradical reagents 24 and 25.
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Doi:10.1007/s10562-013-1156-6
(2014)Doi:10.1007/s10593-013-1387-x
(2013)Doi:10.1016/0022-328X(93)80140-7
(1993)Doi:10.1021/jo9707951
(1997)Doi:10.1039/DT9930000967
(1993)Doi:10.1021/jm00024a009
(1995)