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Volumn 72, Issue 25, 2007, Pages 9582-9589

Singlet oxygen promoted carbon-heteroatom bond cleavage in dibenzyl sulfides and tertiary dibenzylamines. Structural effects and the role of exciplexes

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARBON; ELECTRONS; HYDROGEN; OXYGEN; POSITIVE IONS;

EID: 36849064762     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701641b     Document Type: Article
Times cited : (36)

References (55)
  • 21
    • 36848999212 scopus 로고    scopus 로고
    • 1h They have concluded negatively, but on the basis of a general comparison between sulfides and amines, i.e., not strictly limited to those systems that undergo carbon-heteroatom scission.
    • 1h They have concluded negatively, but on the basis of a general comparison between sulfides and amines, i.e., not strictly limited to those systems that undergo carbon-heteroatom scission.
  • 22
    • 36849000205 scopus 로고    scopus 로고
    • 2k,4b
    • 2k,4b
  • 25
    • 36849028525 scopus 로고    scopus 로고
    • -2 M) was converted to benzylidene cyclohexylamine in 65% yield.
    • -2 M) was converted to benzylidene cyclohexylamine in 65% yield.
  • 26
    • 36849049159 scopus 로고    scopus 로고
    • 2 was formed in a 13% yield, very close to that of the two benzaldehydes (14%).
    • 2 was formed in a 13% yield, very close to that of the two benzaldehydes (14%).
  • 28
    • 36849093851 scopus 로고    scopus 로고
    • For this product study, rose Bengal was preferred to TPP since it allowed us to use shorter irradiation time
    • For this product study, rose Bengal was preferred to TPP since it allowed us to use shorter irradiation time.
  • 29
    • 36849011960 scopus 로고    scopus 로고
    • The same behavior was exhibited by TPP when it was used as the photosensitizer in the photooxidation of 4. A rapid change in color of the solution (from purple to green) was observed and the original color was restored after addition of a base
    • The same behavior was exhibited by TPP when it was used as the photosensitizer in the photooxidation of 4. A rapid change in color of the solution (from purple to green) was observed and the original color was restored after addition of a base.
  • 33
    • 36849060135 scopus 로고    scopus 로고
    • 8
    • 8
  • 37
    • 36849038869 scopus 로고    scopus 로고
    • In principle, also the sulfone yield should be influenced by the substituents. However, the substituent effect on the yield of sulfone can be reasonably neglected given the small yield of mis product with respect to that of the aldehyde. Thus, the effects are probably wimin experimental error
    • In principle, also the sulfone yield should be influenced by the substituents. However, the substituent effect on the yield of sulfone can be reasonably neglected given the small yield of mis product with respect to that of the aldehyde. Thus, the effects are probably wimin experimental error.
  • 39
    • 36849050651 scopus 로고    scopus 로고
    • Calculations, however, favor me zwitterionic structure. 17b,c
    • 17b,c
  • 42
    • 36849090023 scopus 로고    scopus 로고
    • 18b,c
    • 18b,c
  • 45
    • 36849059613 scopus 로고    scopus 로고
    • 1e in MeCN.
    • 1e in MeCN.
  • 46
    • 36849027113 scopus 로고    scopus 로고
    • 1h Apart from this, the mechanism following exciplex formation proposed by Albini and co-workers is different from that presented here.
    • 1h Apart from this, the mechanism following exciplex formation proposed by Albini and co-workers is different from that presented here.
  • 49
    • 36849080735 scopus 로고    scopus 로고
    • It cannot be excluded, however, that formation of the exciplex occurs in a parallel path along with the formation of persulfoxide. Generally, the exciplex undergoes intersystem crossing exclusively, but with substrates with relatively weak α C-H bonds, it might lead to products
    • It cannot be excluded, however, that formation of the exciplex occurs in a parallel path along with the formation of persulfoxide. Generally, the exciplex undergoes intersystem crossing exclusively, but with substrates with relatively weak α C-H bonds, it might lead to products.
  • 50
    • 36849061553 scopus 로고    scopus 로고
    • The fact that in the presence of diphenyl sulfoxide the yield of benzyl sulfoxide becomes close to that of benzaldehyde (Table 5) shows that the conversion of exciplex to persulfoxide is, at least, as important as that leading to benzaldehyde
    • The fact that in the presence of diphenyl sulfoxide the yield of benzyl sulfoxide becomes close to that of benzaldehyde (Table 5) shows that the conversion of exciplex to persulfoxide is, at least, as important as that leading to benzaldehyde.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.