Two fascinating rearrangements through selective placement of bromine substituents, photochemical synthesis of 3-bromo-7-(bromomethyl) tetracyclo[5.3.1.02,6.04,8]undec-10(12)-ene-9,11-dione and its rearrangement with amines

Tetrahedron

Volumn 55, Issue 24, 1999, Pages 7653-7660

  Nair, Mangalam S ^a   Sudhir, Uma ^a   Joly, S ^a   Rath, Nigam P ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

Cage compounds; Photochemistry; Radical and radical reactions; Rearrangement

Indexed keywords

AMINE; BROMINE DERIVATIVE; METHYL GROUP; POLYCYCLIC HYDROCARBON; RADICAL; UNDECANOIC ACID;

ARTICLE; BROMINATION; CHEMICAL BOND; CYCLIZATION; METHYLATION; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033546285     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00381-6     Document Type: Article

References (12)

1. [1] Marchand, A.P. in Aldrichimica Acta, Vol. 28, No. 4, 1995, and references cited therein.
2. [2] Cookson, R.C.; Crundwell, E.; Hill, R.R.; Hudec, J. J.Chem. Soc., 1964, 3062.
3. [3] a) Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M.S. Tetrahedron, 1981, 37, 4543.
4. b) Mehta, G.; Reddy, A. V.; Srikrishna, A. J Chem. Soc. Perkin Trans. 1, 1986, 291.
5. c) Mehta, G.; Srikrishna, A. Chem Rev., 1997, 97, 671.
6. d) Mehta, G.; Rao, K.S. Tetrahedron Lett., 1983, 809.
7. [4] Eaton, P.E.; Or, Y.S.; Branca, J.S. J. Am. Chem. Soc., 1981, 103, 2134.
8. [5] Marchand, A.P.; Ganguly, B.; Mlinaric-Majerski, K.; Veljkovic, J., Tetrahedron, 1998, 54, 11381.
9. [6] Gates, M. J. J. Org. Chem., 1982, 47, 578.
10. [7] The results will be published elsewhere. Typical experimental procedure for bisbromomethylation consisted of sonicating p-dimethoxy benzene in glacial acetic acid with three equivalents of paraformaldehyde and three equivalents of 33% HBr in glacial acetic acid for one hour. This gave the 2,5-(bisbromomethyl)-1,4-dimethoxybenzene in 65% yield. Similarly by using concentrated hydrochloric acid instead of HBr we obtained 2,5-(bischloromethyl)-1,4-dimethoxybenzene in 68% yield.
11. [8] Witiak, D. T.; Loper, J. T.; Ananthan, S.; Almerico, A. M.; Verhoef, V. L.; Filppi, J.A. J.Med. Chem., 1989, 32, 1636.
12. [9] Pitre, S.; M.Sc. thesis submitted to the University of Hyderabad; unpublished results with Mehta, G. This has also been repeated in our laboratory.