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Platinum Complexes of Aromatic Selenolates
Author(s) -
Fuller Amy L.,
Knight Fergus R.,
Slawin Alexandra M. Z.,
Woollins J. Derek
Publication year - 2010
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201000357
Subject(s) - chemistry , naphthalene , diselenide , medicinal chemistry , selenium , platinum , stereochemistry , halogenation , alkylation , ring (chemistry) , organic chemistry , catalysis
Several synthetic methods are used to prepare naphthalene‐based aromatic 1,2‐diselenoles. A new one‐pot synthesis starting from naphthalene is used to produce theknown compound naphtho[1,8‐ c , d ][1,2]diselenole (Se 2 naph).Friedel–Crafts alkylation is used on Se 2 naph to substitute either one tert ‐butyl group to form 2‐ tert ‐butylnaphtho[1,8‐ c , d ][1,2]diselenole (mt‐Se 2 naph) or two tert ‐butyl groups to form 2,7‐di‐ tert ‐butylnaphtho[1,8‐ c , d ][1,2]diselenole (dt‐Se 2 naph). Bromination of mt‐Se 2 naph results in dibromination of the naphthalene ring, rather than reaction at selenium, to give 4,7‐dibromo‐2‐ tert ‐butylnaphtho[1,8‐ c , d ][1,2]diselenole (mt‐Se 2 naphBr 2 ). Reduction of the Se–Se bond in Se 2 naph, mt‐Se 2 naph, dibenzo[ c , e ][1,2]diselenine (dibenzSe 2 ), or diphenyl diselenide (Se 2 Ph 2 ) with LiBEt 3 H, followed by in‐situ addition of [PtCl 2 {P(OPh) 3 } 2 ] yields the four‐coordinate mono‐ and dinuclear platinum(II) bis(phosphite) complexes [Pt( Se 2 naph ){P(OPh) 3 } 2 ] ( 1 ), [Pt( mt‐Se 2 naph ){P(OPh) 3 } 2 ] ( 2 ), [Pt 2 ( dibenzSe 2 ) 2 {P(OPh) 3 } 2 ] ( 3 ), cis ‐[Pt( SePh ) 2 {P(OPh) 3 } 2 ] ( 4 ), and trans ‐[Pt 2 ( SePh ) 4 {P(OPh) 3 } 2 ] ( 5 ).