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An Efficient Method for Synthesizing Substituted Naphtho‐1,3‐dithiole‐2‐thiones from Tetrachlorotetrathionaphthalene and Sodium Trithiocarbonate
Author(s) -
Fanghänel Egon,
Ullrich Andreas,
Wagner Christoph
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199808)1998:8<1577::aid-ejoc1577>3.0.co;2-5
Subject(s) - chemistry , sodium , dithiol , medicinal chemistry , mercury (programming language) , benzoquinone , inorganic chemistry , polymer chemistry , organic chemistry , programming language , computer science
Two types of naphtho‐fused 1,3‐dithiole‐2‐thiones ( 2a – f and 4a – d ) were obtained by the reaction of 3,4,7,8‐tetrachloro‐naphtho[1,8‐ cd :5,6‐ c′d′ ]bis(1,2‐dithiole) ( 1 ) and sodium trithiocarbonate. The dechalcogenization of the thiones, using mercury acetate, leads to the corresponding naphtho‐1,3‐dithiol‐2‐ones ( 3a – d and 5a – d ). The structures of 3a and 4a were confirmed by X‐ray investigation. The tetrathiafulvalenes (TTFs) 6 and 7 were synthesized from 2d and 3c by coupling of the starting compounds with the help of triethyl phosphite. Using 2,3‐dichloro‐5,6‐dicyano‐benzoquinone (DDQ) the TTFs were converted into semiconducting charge‐transfer complexes.