Photochemical cycloisomerizations via 7-exo-dig reactions on a calix[4]arene scaffold

Journal of Organic Chemistry

Volumn 72, Issue 12, 2007, Pages 4532-4535

  Al Saraierh, Hassan ^a   Miller, David O ^a   Georghiou, Paris E ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOISOMERIZATIONS; OXACYCLIC SYSTEMS; PHOTOLABILE;

CYCLIZATION; ISOMERIZATION; PHOTOCHEMICAL REACTIONS;

ORGANIC CHEMICALS;

1,3 BIS(PHENYLETHYNYL) 4 TERT BUTYLCALIX[4]ARENE DERIVATIVE; CALIXARENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; MATRIX ATTACHMENT REGION; PHOTOCHEMISTRY;

EID: 34250172381     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070236m     Document Type: Article

References (22)

1. For recent monographs, see: (a) Gutsche, C. D. In Calixarenes Revisited, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1998.
2. (b) Calixarenes2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001.
3. Calixarenes in Action; Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, England, 2000.
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14. X-ray crystallographic data of 7 are included with the Supporting Information and in cif format.
15. A seven-membered oxacycle formed by radical-initiated 7-exo-dig cyclization has been reported by Grigg et al., in which the exocyclic alkene formed has the E configuration and is analogous to the structure of the putative labile isomers 11 and 12 proposed herein. See: Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479-11502.
16. -1 in favor of 7.
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22. -1 in favor of 7.