Facile synthesis of 2,3-diiodonaphthalene and 2-bromo-3-iodonaphthalene

Synthetic Communications

Volumn 33, Issue 15, 2003, Pages 2751-2756

  Hellberg, Jonas ^a   Allared, Fredrik ^a   Pelcman, Margit ^a,b  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b BIOVITRUM AB   (Sweden)

Author keywords

2,3 Diiodonaphthalene; 2 Bromo 3 iodonaphthalene; Iodination; Retro Diels Alder

Indexed keywords

2 BROMO 3 IODONAPHTHALENE; 2,3 DIIODONAPHTHALENE; ALKADIENE; BIS(HEXACHLOROCYCLOPENTADIENE); MESYLIC ACID; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; IODINATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0042063883     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021997     Document Type: Article

References (12)

1. Grützmacher, H.F.; Lohmann, J. Nachweis von isomeren dehydronaphthalinen durch pyrolyse-massenspektrometrie. Liebigs Ann. Chem. 1970, 733, 88.
2. Perry, R.J.; Turner, S.R. Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. J. Org. Chem. 1991, 56, 6573.
3. Cambell, I.D.; Eglinton, G. A novel photochemical cyclisation of o-bisiodoethynylbenzene to substituted naphthalenes. J. Chem. Soc. C 1968, 2120.
4. Ward, E.R.; Pearson, B.D. The synthesis of 2:3-6:7-dibenzodiphenylene, and a note on the reaction of 1-bromo-2-iodonaphthalene with magnesium. J. Chem. Soc. 1959, 1676.
5. Hellberg, J.; Pelcman, M. Synthesis of anullated dioxins and their use as donors for cation radical salts. Tetrahedron Lett. 1994, 35, 1769.
6. Look, M. Hexachlorocyclopentadiene adducts of aromatic compounds and their reaction products. Aldrichimica Acta 1974, 7, 23.
7. Jaud, Chanon. Tandem Diels-Alder-Diels-Alder reaction displaying high stereoselectivity: reaction of hexachlorocyclopentadiene with naphthalene. Acta Chem. Scand. 1993, 47, 92.
8. Merkushev, E.B. Advances in the synthesis of iodoaromatic compounds. Synthesis 1988, 923.
9. Suzuki, H. Direct iodination of polyalkylbenzenes: iododurene. Org. Synth. Coll. 1988, Vol. VI, 700.
10. Suzuki, H. The direct iodination of polyalkylbenzenes bearing bulky groups. Bull. Chem. Soc. Jap. 1966, 39, 128.
11. Mattern, D.L. Periodination of benzene with periodate/iodide. J. Org. Chem. 1983, 48, 4772.
12. Mattern, D.L. Direct polyiodination of benzenesulfonic acid. J. Org. Chem. 1991, 56, 5903.