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4.5.6.7- Tetrahydrobenzo thio phene

Friedel-Crafts acylation of dibenzothiophene with succinic anhydride is known to occur in the 2-position, yielding y-oxo-2-dibenzothiophene-but3Tic acid (135a). Subsequent Wolff-Kishner reduction and internal cyclization yields 7-keto-7,8,9,10-tetrahydrobenzo[6]naphtho[2,3-d]thio-phene (136a). - This reaction has been extended to 4-methyldibenzo-... [Pg.277]

Fig. 29. Correlation between relative hydrogenolysis reactivity and the electron densities on sulfur. ( ) Reaction conditions 300°C, 71 atm, sulfided CoO-Mo03/A1203 (5). (1) DBT (2) benzo[fo]naphtho[2,3-4]thiophene (3) 7,8,9,10-tetrahydrobenzo[b]naphtho[2,3-rf]thio-phene (4) 5b,6,ll,lla-tetrahydrobenzo[fc]naphtho[2,3-d]thiophene. (O) Reaction conditions 450°C, 1 atm, sulfided CoO-Mo03/A1203(6). (5) Thiophene (6) tetrahydrothiophene (7) benzothiophene (8) 2,3-dihydrobenzothiophene. ( + ) Reaction conditions 360°C, 2.9 MPa, sulfided NiO-Mo03/Al203(3). (9) 1-Methyl-DBT (10) 2- or 3-methyl-DBT (11) 4-methyl-DBT (12) 4,6-dimethyl-DBT. (A) Reaction conditions 300°C, 102 atm, sulfided CoO-Mo03/ Al203(8). (13) 2,8-Dimethyl-DBT (14) 3,7-dimethyl-DBT (15) 4-methyl-DBT (16) 4,6-di-methyl-DBT. Reprinted with permission from Ref. 38, Ma et al. (1995). Copyright 1995 American Chemical Society. Fig. 29. Correlation between relative hydrogenolysis reactivity and the electron densities on sulfur. ( ) Reaction conditions 300°C, 71 atm, sulfided CoO-Mo03/A1203 (5). (1) DBT (2) benzo[fo]naphtho[2,3-4]thiophene (3) 7,8,9,10-tetrahydrobenzo[b]naphtho[2,3-rf]thio-phene (4) 5b,6,ll,lla-tetrahydrobenzo[fc]naphtho[2,3-d]thiophene. (O) Reaction conditions 450°C, 1 atm, sulfided CoO-Mo03/A1203(6). (5) Thiophene (6) tetrahydrothiophene (7) benzothiophene (8) 2,3-dihydrobenzothiophene. ( + ) Reaction conditions 360°C, 2.9 MPa, sulfided NiO-Mo03/Al203(3). (9) 1-Methyl-DBT (10) 2- or 3-methyl-DBT (11) 4-methyl-DBT (12) 4,6-dimethyl-DBT. (A) Reaction conditions 300°C, 102 atm, sulfided CoO-Mo03/ Al203(8). (13) 2,8-Dimethyl-DBT (14) 3,7-dimethyl-DBT (15) 4-methyl-DBT (16) 4,6-di-methyl-DBT. Reprinted with permission from Ref. 38, Ma et al. (1995). Copyright 1995 American Chemical Society.
Tetrahydrobenzo[6]thiophene103 and several benzo[6]thio-phenes containing electron-donating substituents, e.g., 5,6-dimeth-oxy,180 5,6-methylenedioxy,180 6-ethoxy,424 3-methoxy,183 and 3-methyl,487 are smoothly brominated in the 2-position by iV-bromo-succinimide in carbon tetrachloride or chloroform in the absence of peroxides. Similar treatment of 2-methoxybenzo[6]thiophene gives the 3-bromo derivative.183... [Pg.265]

Hydroxybenzo[6]thiophene has been isolated from coal tar.42 It may be prepared by dehydrogenation of 4,5,6,7-tetrahydrobenzo-[6]thiophen-4-one (Section VI,B, 4), and from 4-aminobenzo[6]thio-phene by standard procedures.422... [Pg.306]

Dihydrobenzo[6]thiophene undergoes acetylation 192,427 and succinoylation 426 in the 5-position. 4,5,6,7-Tetrahydrobenzo[6]thio-phene is acylated in the 2-position,193,194,436,439,440 or, when this is occupied by an alkyl group, in the 3-position.194,436... [Pg.331]

See other pages where 4.5.6.7- Tetrahydrobenzo thio phene is mentioned: [Pg.255]    [Pg.342]    [Pg.342]   
See also in sourсe #XX -- [ Pg.27 ]



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