Synthesis of Unsymmetrical Tetrathiafulvalene Derivatives via Me(3)Al-Promoted Reactions of Organotin Compounds with Esters.
Efficient synthetic methods for the construction of a wide variety of unsymmetrical tetrathiafulvalenes (TTFs) via the Me(3)Al-promoted reactions of organotin thiolates or selenolates with esters are described. Reaction of tin thiolates (3a-c and 10) and selenolates (3d, 5, and 7) with esters (11a,b) in the presence of Me(3)Al as a Lewis acid gave dihydrotetrathiafulvalene derivatives (12, 14, 15, and 17-20) and 1,3-dithiane derivatives (13 and 16). In addition, the synthesis of diselenadithiafulvalene derivatives (25-28) could be accomplished by Me(3)Al-mediated reaction of tin thiolate (2a) or selenolates (3d and 5) with esters (22a, 22d, and 24). Furthermore, the application of the Me(3)Al-promoted reaction of tin thiolate (34) with esters (11a-b, 22a-d, and 35a-b) for the synthesis of unsymmetrical TTFs-fused donors enabled us to obtain various TTFs-fused systems (29-33) in short steps.
Yamada Ji
Jun-ichi
Department of Material Science, Faculty of Science, Himeji Institute of Technology, 1479-1 Kanaji Kamigori-cho, Ako-gun, Hyogo 678-12, Japan.
Satoki
Shyûji
S
Mishima
Sachinori
S
Akashi
Nobutaka
N
Takahashi
Kouhei
K
Masuda
Nobuyuki
N
Nishimoto
Yasushi
Y
Takasaki
Satoshi
S
Anzai
Hiroyuki
H