Photochemical release of amines by C,N-bond cleavage

Synlett

Volumn , Issue 4, 2003, Pages 501-504

  Schoenleber, Ralph O ^a   Giese, Bernd ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Amine; Coumarin; Photocleavage; Solid support

Indexed keywords

AMINE; COUMARIN;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; PHOTOCHEMICAL QUENCHING; PHOTOCHEMISTRY; PHOTOLYSIS; PROTON TRANSPORT; TECHNIQUE;

EID: 0037237281     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37507     Document Type: Article

References (39)

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18. 3 were determined by RP-HPLC. The influence of H-donors was checked by adding 50 equiv 1,4-cyclohexadiene or n-decanethiol before irradiation.
19. 4 and concentrated under reduced pressure, yielding 16.6 mg (0.123 mmol, 85%) of amine 2a.
20. 24
21. C,N-Cleavage at the solid support (12→2a): Photolyses in quartz glass cells (500 W Hg high-pressure lamp fitted with a 360 nm cutoff filter) were conducted with about 20 mg of resin 12 suspended in 2.5 mL of methanol in the presence of n-decanethiol (100 equiv). In order to stabilize the cleaved off amine 2a 1 M HCl (1.5 equiv) was added. The cells were maintained at 20°C and irradiated for 3 hours with gentle mixing of the beads by means of a magnetic stirrer. After photolysis, the supernatant was analyzed by reversed-phase HPLC using an internal standard. The amount of cleaved amine 2a was 80%, based on the loading of resin 12.
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27. 3 In a similar way, the addition of large amounts of acids to 1 retarded or even inhibited the photocleavage.
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