89. Benzcyclooctatetraenes. Part III. Diphenylene and tetraphenylene

Rapsōn, W. S.; Shuttleworth, R. G.; Niekerk, J. N. van

doi:10.1039/jr9430000326

Cited by 89 publications

(43 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Tetraphenylene (1) [1] is a structurally highly interesting molecule with a ground state D 2d geometry and with a distinct saddle-shaped structure [2,3] in which all the benzene rings are orientated above and below the average plane of the molecule ( Figure 1). …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiopure (S,R,S)‐ and (R,S,R)‐1,4,5,8,9,16‐Hexahydroxytetraphenylenes

Hau

Wong

2007

Adv Synth Catal

View full text Add to dashboard Cite

Scheme 3. Synthesis of racemic 5 from 11. a) PhIA C H T U N G T R E N N U N G (OAc) 2 , CH 3 CN, H 2 O, 0 8C, 2 h, 48 % for 12, 22 % for 13; b) Zn, AcOH, room temperature, 7 h, 74 %; c) BBr 3 , CH 2 Cl 2 , 08C to room temperature, 12 h, 90 %.Scheme 4. Synthesis of (S,R,S)-5. a) CH 3 I, K 2 CO 3 , acetone, reflux, 3 h, 100 %; b) i) 2.2 equivs. BBr 3 , CH 2 Cl 2 , 08C, 15 min; ii) 2.2 equivs. Tf 2 O, pyridine, CH 2 Cl 2 , 10 h, 27 %; c) NaOH, dioxane, methanol, 60 8C, 12 h, 98 %; d) i) PhIA C H T U N G T R E N N U N G (OAc) 2 , CH 3 CN, H 2 O, 0 8C, 2 h; ii) Zn, AcOH, room temperature, 7 h, 36 %; e) BBr 3 , CH 2 Cl 2 , 08C to room temperature, 12 h, 90 % Scheme 5. Synthesis of (R,S,R)-5. a) CH 3 I, K 2 CO 3 , acetone, reflux, 3 h, 100 %; b) i) 2.2 equivs. BBr 3 , CH 2 Cl 2 , 08C, 15 min; ii) 2.2 equivs. Tf 2 O, pyridine, CH 2 Cl 2 , 10 h, 27 %; c) NaOH, dioxane, methanol, 60 8C, 12 h, 97 %; d) i) PhIA C H T U N G T R E N N U N G (OAc) 2 , CH 3 CN, H 2 O, 0 8C, 2 h; ii) Zn, AcOH, room temperature, 7 h, 34 %; e) BBr 3 , CH 2 Cl 2 , 08C to room temperature, 12 h, 92 %.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of Enantiopure (S,R,S)‐ and (R,S,R)‐1,4,5,8,9,16‐Hexahydroxytetraphenylenes

Hau

Wong

2007

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…However, to date no methods have been described for the realization of 1 by direct polymerization of benzyne. The first synthesis of 1 was reported by Rapson et al in 1943 via a copper-assisted coupling of a Grignard reagent (Scheme 1) [11]. Since then, numerous approaches towards tetraphenylenes have been documented [6][7][8][9][10].…”

Section: Direct Synthesis Of Tetraphenylenesmentioning

confidence: 99%

“…After tetraphenylene (1) was realized, Rapson et al immediately proceeded to perform nitration and bromination reactions on 1 to give monobromo-and tetranitro-tetraphenlene derivatives (Scheme 37) [11]. However, the substituted positions of these products could not be determined easily.…”

Section: Direct Electrophilic Aromatic Substitution Of Tetraphenylenesmentioning

confidence: 99%

“…Following flourishing research over many decades, the coupling reaction accessible via organometallic reagents nowadays has many more possible applications. The first synthesis of tetraphenylene, as previously mentioned, was a homo-coupling reaction of Grignard reagents [11]. Soon after, Wittig prepared o-dilithiobenzene and 2,2 -dilithiobiphenyl from o-phenylenemercury (by treatment of o-dibromobenzene with sodium mercury amalgam).…”

Section: Oxidative Coupling Reaction Of Dilithiobiphenyl Derivativesmentioning

confidence: 99%

“…Considering the classical mechanism of Reppe cyclization for COT catalyzed by nickel [16,17], Johnson isolated an asymmetric nickel-nickel bonded intermediate (11) in the reaction of 5 with bis(1,5-cyclooctadiene)nickel and a larger phosphine i-Pr 3 P. The solid-state crystallographic structures of dinuclear species (10) (R = i-Pr) and (11) support their role in a mechanism involving a formal Ni(III)-Ni(I) complex (Scheme 5) [18].…”

Section: Pyrolysis And/or Metal-catalyzed Dimerization Of Biphenylenesmentioning

confidence: 99%

See 2 more Smart Citations