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Volumn 49, Issue 25, 2008, Pages 4043-4046

Photoinduced highly selective thiophosphination of alkynes using a (PhS)2/(Ph2P)2 binary system

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CHLOROFORM; DIPHENYL DISULFIDE; PHENYLACETYLENE; PHOSPHINE DERIVATIVE; SULFIDE; TETRAPHENYLDIPHOSPHINE; XENON;

EID: 43449088244     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.068     Document Type: Article
Times cited : (39)

References (39)
  • 1
    • 14744290401 scopus 로고    scopus 로고
    • Yamamoto H., and Oshima K. (Eds), Wiley-VCH, Weinheim
    • Ogawa A. In: Yamamoto H., and Oshima K. (Eds). Main Group Metals in Organic Synthesis Vol. 2 (2004), Wiley-VCH, Weinheim 813
    • (2004) Main Group Metals in Organic Synthesis , vol.2 , pp. 813
    • Ogawa, A.1
  • 2
    • 33947335344 scopus 로고
    • Bisthiolation of alkynes:
    • Bisthiolation of alkynes:. Heiba E.I., and Dessau R.M. J. Org. Chem. 32 (1967) 3837
    • (1967) J. Org. Chem. , vol.32 , pp. 3837
    • Heiba, E.I.1    Dessau, R.M.2
  • 3
    • 33845278103 scopus 로고
    • Bisselenation of alkynes:
    • Bisselenation of alkynes:. Back T.G., and Krishna M.V. J. Org. Chem. 53 (1988) 2533
    • (1988) J. Org. Chem. , vol.53 , pp. 2533
    • Back, T.G.1    Krishna, M.V.2
  • 28
    • 43449109114 scopus 로고    scopus 로고
    • During the contribution of this Letter in this journal, thiophosphination of terminal alkynes with thiophosphines using radical initiator has been reported:
    • During the contribution of this Letter in this journal, thiophosphination of terminal alkynes with thiophosphines using radical initiator has been reported:. Wada T., Kondoh A., Yorimitsu H., and Oshima K. Org. Lett. 10 (2008) 1155
    • (2008) Org. Lett. , vol.10 , pp. 1155
    • Wada, T.1    Kondoh, A.2    Yorimitsu, H.3    Oshima, K.4
  • 29
    • 43449086636 scopus 로고    scopus 로고
    • note
    • Our preliminary results of this photoinduced thiophosphination and relating works were presented at the 87th Annual Meeting of Chemical Society of Japan (March 26, 2007, Suita, Osaka, Japan) and the 34th Symposium on Main Group Element Chemistry (December 15, 2007, Osaka, Japan).
  • 30
    • 43449128025 scopus 로고    scopus 로고
    • note
    • The isolation of 4a was difficult, due to the sensitivity of 4a toward air-oxidation.
  • 31
    • 43449086951 scopus 로고    scopus 로고
    • note
    • 20BrOPS: C, 63.55; H, 4.10. Found: C, 63.56; H, 4.10.
  • 32
    • 43449103299 scopus 로고    scopus 로고
    • note
    • max = 40; Troy, D.; Turpin, R.; Voigt, D. Bull. Soc. Chim. Fr. 1979, 241.
  • 33
    • 43449091213 scopus 로고    scopus 로고
    • note
    • 31P NMR spectrum.
  • 34
    • 43449121483 scopus 로고    scopus 로고
    • note
    • 2 is conceivably a very fast process. Accordingly, the present thiophosphination of alkynes requires continuous photoirradiation during the reaction.
  • 35
    • 0344932373 scopus 로고
    • In the cases of aliphatic acetylene, prolonged reaction time was required. This is because α-aryl-substituted vinylic radicals are assumed to be π-radicals and more stable than alkyl-substituted vinylic σ-radicals. See:
    • In the cases of aliphatic acetylene, prolonged reaction time was required. This is because α-aryl-substituted vinylic radicals are assumed to be π-radicals and more stable than alkyl-substituted vinylic σ-radicals. See:. Singer L.A., and Chen J. Tetrahedron Lett. 10 (1969) 4849
    • (1969) Tetrahedron Lett. , vol.10 , pp. 4849
    • Singer, L.A.1    Chen, J.2
  • 36
    • 43449125826 scopus 로고    scopus 로고
    • note
    • 2: 470.1292, found: 470.1299.
  • 38
    • 43449102132 scopus 로고    scopus 로고
    • note
    • 2: C, 65.93; H, 5.89. Found: C, 65.90; H, 5.92.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.