Synthesis and liquid membrane transport properties of photolabile molecular clips based on dithiane-spiro-crown ethers

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2633-2635

  Barnhurst, Loren A ^a   Kutateladze, Andrei G ^a  

^a UNIVERSITY OF DENVER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; PARAQUAT;

ARTICLE; ARTIFICIAL MEMBRANE; CHEMISTRY; PHOTOCHEMISTRY; SYNTHESIS;

ETHERS; MEMBRANES, ARTIFICIAL; PARAQUAT; PHOTOCHEMISTRY;

EID: 0035940139     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016309k     Document Type: Article

References (10)

1. For selected examples of bis-crown-based ionophores, see: Bühl-mann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593.
2. Photoinduced cleavage in hydroxy-or amino-alkyl dithianes: (a) McHale, W. A.; Kutateladze, A. G. J. Org. Chem. 1998, 63, 9924.
3. (b) Wan, Y.; Mitkin, O.; Barnhurst, L.; Kurchan, A.; Kutateladze, A. Org. Lett. 2000, 2, 3817.
4. (c) Vath, P.; Falvey, D. E.; Barnhurst, L. A.; Kutateladze, A. G. J. Org. Chem. 2001, 66, 2886.
5. (d) Mitkin, O. D.; Kurchan, A. N.; Wan, Y.; Schiwal, B.-F.; Kutateladze, A. G. Org. Lett. 2001, 3, 1841.
6. +, 30), 144 (60), 98 (100), 85 (60).
7. 2 = 6.8 Hz, 2H), 3.53-3.62 (m, 32H), 3.44 (s, 2H), 2.70-2.78 (m, 4H), 2.52-2.58 (m, 4H).
8. For further mechanistic details of the photocleavage, see refs 2a,c.
9. 4. The progress was monitored by the increase in UV absorption of the receiving solution at λ = 256 nm.
10. Judging by NMR, the photofragmentation was driven to >90% conversion. At this point we can only speculate on the nature of the residual transferability by irradiated 10. One possibility is that overoxidation of the dithiane moiety in the released mono-crown ether 7 produces a small amount of a better complexing byproduct.