TY - JOUR
T1 - Large PAHs by reductive peri-peri "dimerization" of phenalenones
AU - Pogodin, Sergey
AU - Agranat, Israel
PY - 1999/11/4
Y1 - 1999/11/4
N2 - (formula presented) Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl4/LiAlH4/THF) gave peropyrene (1), tetrabenzo[a,Cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2′,1′,8′,7′-opqr] pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri-peri "dimerization" of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D2h-1, the most stable conformation, resembles the Clar picture of 1.
AB - (formula presented) Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl4/LiAlH4/THF) gave peropyrene (1), tetrabenzo[a,Cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2′,1′,8′,7′-opqr] pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri-peri "dimerization" of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D2h-1, the most stable conformation, resembles the Clar picture of 1.
UR - http://www.scopus.com/inward/record.url?scp=0001755169&partnerID=8YFLogxK
U2 - 10.1021/ol9909435
DO - 10.1021/ol9909435
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AN - SCOPUS:0001755169
SN - 1523-7060
VL - 1
SP - 1387
EP - 1390
JO - Organic Letters
JF - Organic Letters
IS - 9
ER -