Premium
The First Synthesis and Isolation of ‘Bis(aryloxy)phosphorothioylsulfenyl Iodides' (=Bis(aryloxy)phosphinesulfenyl Iodide P ‐Sulfides) from the Reaction of S , S ′‐(Diphenylstannylene) O , O , O ′, O ′‐Tetraaryl Bis[phosphorodithioates] (=[(Diphenylstannylene)bis(thio)]bis[bis(aryloxy)phosphine P ‐Sulfides]) with N ‐Iodosuccinimide
Author(s) -
Shi Min,
Kato Shinji
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200208)85:8<2559::aid-hlca2559>3.0.co;2-9
Subject(s) - chemistry , reagent , iodide , adduct , medicinal chemistry , electrophile , thio , cyclohexene , organic chemistry , catalysis
S , S ′‐(Diphenylstannylene) O , O , O ′, O ′‐tetraaryl bis[phosphorodithioates] (=[(diphenylstannylene)bis(thio)]bis[bis(aryloxy)phosphine P ‐sulfides]) 5 react with N ‐iodosuccinimide (NIS) in CH 2 Cl 2 at −30° under A to give ‘bis(aryloxy)phosphorothioylsulfenyl iodides' (=bis(aryloxy)phosphinesulfenyl iodide P ‐sulfides) 6 ( Scheme 3 ), which can readily react in situ with 4‐methylbenzenecarbodithioic acid, thiol, and cyclohexene to afford the corresponding unsymmetrical disulfides and the adduct in good yields as the novel electrophilic dithiophosphorylating reagents ( Schemes 4 and 5 ). By adding hexane into the solution at −30° after reaction of 5 with NIS, the ‘phosphorothioylsulfenyl iodides' 6 can be isolated as yellow solids in good yields (see Table ).