Orthocyclophanes. 5.1 functionalization of [16] starand on the aromatic ring

Bulletin of the Korean Chemical Society

Volumn 17, Issue 6, 1996, Pages 558-560

  Lim, Choon Woo ^a   Hong, Jong In ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0542418100     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (8)

1. Lee, W. Y.; Park, C. H.; Kim, E. H. Orthocyclophanes. 4. Functionalization of [1n]Orthocyclophanes on the Aromatic Rings. J. Org. Chem. 1994, 59, 4495.
2. (a) Lee, W. Y.; Park. C. H.; Kim, S. J. Am. Chem. Soc. 1993, 115, 1184.
3. (b) Lee, W. Y.; Park, C. H. J. Org. Chem. 1993, 58, 7149.
4. (c) Lee, W. Y. Synlett, 1994, 765.
5. Gokel, G. W.; Trafton, J. E. Cation Binding by Lariat Ethers. In Cation Binding by Macrocycles, Inoue, Y.; Gokel, G. W. Ed.; Marcel Dekker, Inc.: New York and Basel, 1990; pp 253-310.
6. Reduction of 4-methylphthalic anhydride with LAH followed by monobromination of the resulting l,2-bis(hydroxymethyl)-4-methylbenzene with HBr in benzene gave rise to two isomeric benzyl alcohols, 2-(bromomethyl)-4-methy-Ibenzyl alcohol and 2-(bromomethyl)-5-methylbenzyl alcohol, which were protected with dihydropyran in the presence of catalytic amounts of p-TsOH to give 1a and 1b (69% overall yidle from l,2-bis(hydroxymethyl)-4-methyl-benzene).
7. The precursor of the dilithio reagent 7, bis(2-bromophenyl)methane was prepared by modification of the literature procedures: Lee, W. Y.; Park, C. H.; Kim, Y. D. J. Org. Chem. 1992, 57, 4074 and references therein.
8. Trahanovsky, W. S.; Young, L. B. J. Org. Chem. 1966, 31, 2033.