[2.2]Metacyclophanes having hydroxy groups on the bridge

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3745-3746

  Sahade, Daniel A ^a   Mataka, Shuntaro ^a   Sawada, Tsuyoshi ^a   Tsukinoki, Takehito ^b   Tashiro, Masashi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METACYCLOPHANE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030952729     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00743-0     Document Type: Article

References (8)

1. a) Wirth, T. Angew. Chem. Int. Ed. Eng. 1996, 35, 61-63.
2. b) Khurana, J. M.; Sehgal, A.; Gogia, A.; Manian, A.; Maikap, G. C. J. Chem Soc., Perkin Trans.1, 1996, 2213-2215.
3. c) Tsukinoki, T.; Ishimoto, K.; Suzuki, H.; Mataka, S.; Tashiro, M. Bull. Chem. Soc. Jpn. 1993, 66, 3419-3422.
4. Grützmacher, H. F.; Neumann, E. Chem. Ber. 1993, 126, 1495-1497.
5. General procedure: Aluminium powder (150 mesh) was added to a solution of dialdehyde in methanol. The mixture was subjected to mechanical stirring and then the aqueous NaOH solution was added dropwise during a period of 15 min. Stirring was continued for 3 h. The mixture was filtered and the filtrate was extracted with ethyl acetate. The extract was washed with water, dried (magnesium sulfate) and evaporated to afford the crude product which was column chomatographed (silica gel, Wako C-300, eluant: hexane/ethyl acetate mixtures) to give a mixture of cyclophane and oligomers. The mixture was washed with dichloromethane to give the cyclophane. Compounds 3 and 6 gave satisfactory elemental analysis.
6. +).
7. w= 0.1746.
8. Altomare, M.; Burla, M.; Camalli, G.; Cascarano, C.; Giacovazzo, A.; Guagliardi, G.; Polidori, J. J. Appl. Cryst. 1993, 26, 343-350.