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Fifty years of (benz)oxaphospholene chemistry

(2017) CHEMISTRY-A EUROPEAN JOURNAL. 23(69). p.17413-17431
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Abstract
The first synthesis of benzoxaphospholenes dates back to the 1960s. Since then, the structural variety of reported (benz)oxaphospholenes has steadily increased. Organophosphorus compounds have caught the interest of synthetic chemists for a couple of decades now because of their interesting biological properties. Oxaphospholenes, in particular, could serve as carbohydrate mimetics, and benzoxaphospholenes have been reported to possess bactericidal, insecticidal, herbicidal, and fungistatical properties. Transesterification reactions and addition of phosphorus nucleophiles to carbonyl compounds were reaction types that led to the production of the first (benz)oxaphospholenes. When it was discovered that allenylphosphonates could easily be obtained from propargyl alcohols and dialkyl halophosphites, the electrophile-induced cyclization reaction of these allenylphosphonate precursors resulted in a huge boom in the amount of reports on oxaphospholene synthesis. To this day, this method is still frequently used. Ring-closing metathesis and Horner-Wadsworth-Emmons reactions have also proven their potential for the preparation of oxaphospholenes. In recent years, Pd, Rh and Au-catalysis have made their entry, generating (benz)oxaphospholenes from a wide variety of simple substrates. A couple of miscellaneous methods are summarized at the end of the Review.
Keywords
allenes, benzoxaphospholenes, cyclization, oxaphospholenes, phosphorus heterocycles, RING-CLOSING METATHESIS, 1, 2-ALKADIENEPHOSPHONIC DIALKYL ESTERS, 1, 2-ALLENYL PHOSPHONIC-ACIDS, BIFUNCTIONALIZED ALLENES, PHOSPHORYLATED ALLENES, SULFENYL CHLORIDES, 1, 2-OXAPHOSPHOL-3-ENE DERIVATIVES, POTASSIUM DICHLOROIODATE(I), INTRAMOLECULAR CYCLIZATION, ELECTROPHILIC CYCLIZATION

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Citation

Please use this url to cite or link to this publication:

MLA
Berton, Jan, Thomas Heugebaert, David Virieux, et al. “Fifty Years of (benz)oxaphospholene Chemistry.” CHEMISTRY-A EUROPEAN JOURNAL 23.69 (2017): 17413–17431. Print.
APA
Berton, J., Heugebaert, T., Virieux, D., & Stevens, C. (2017). Fifty years of (benz)oxaphospholene chemistry. CHEMISTRY-A EUROPEAN JOURNAL, 23(69), 17413–17431.
Chicago author-date
Berton, Jan, Thomas Heugebaert, David Virieux, and Christian Stevens. 2017. “Fifty Years of (benz)oxaphospholene Chemistry.” Chemistry-a European Journal 23 (69): 17413–17431.
Chicago author-date (all authors)
Berton, Jan, Thomas Heugebaert, David Virieux, and Christian Stevens. 2017. “Fifty Years of (benz)oxaphospholene Chemistry.” Chemistry-a European Journal 23 (69): 17413–17431.
Vancouver
1.
Berton J, Heugebaert T, Virieux D, Stevens C. Fifty years of (benz)oxaphospholene chemistry. CHEMISTRY-A EUROPEAN JOURNAL. 2017;23(69):17413–31.
IEEE
[1]
J. Berton, T. Heugebaert, D. Virieux, and C. Stevens, “Fifty years of (benz)oxaphospholene chemistry,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 23, no. 69, pp. 17413–17431, 2017.
@article{8545196,
  abstract     = {The first synthesis of benzoxaphospholenes dates back to the 1960s. Since then, the structural variety of reported (benz)oxaphospholenes has steadily increased. Organophosphorus compounds have caught the interest of synthetic chemists for a couple of decades now because of their interesting biological properties. Oxaphospholenes, in particular, could serve as carbohydrate mimetics, and benzoxaphospholenes have been reported to possess bactericidal, insecticidal, herbicidal, and fungistatical properties. Transesterification reactions and addition of phosphorus nucleophiles to carbonyl compounds were reaction types that led to the production of the first (benz)oxaphospholenes. When it was discovered that allenylphosphonates could easily be obtained from propargyl alcohols and dialkyl halophosphites, the electrophile-induced cyclization reaction of these allenylphosphonate precursors resulted in a huge boom in the amount of reports on oxaphospholene synthesis. To this day, this method is still frequently used. Ring-closing metathesis and Horner-Wadsworth-Emmons reactions have also proven their potential for the preparation of oxaphospholenes. In recent years, Pd, Rh and Au-catalysis have made their entry, generating (benz)oxaphospholenes from a wide variety of simple substrates. A couple of miscellaneous methods are summarized at the end of the Review.},
  author       = {Berton, Jan and Heugebaert, Thomas and Virieux, David and Stevens, Christian},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {allenes,benzoxaphospholenes,cyclization,oxaphospholenes,phosphorus heterocycles,RING-CLOSING METATHESIS,1,2-ALKADIENEPHOSPHONIC DIALKYL ESTERS,1,2-ALLENYL PHOSPHONIC-ACIDS,BIFUNCTIONALIZED ALLENES,PHOSPHORYLATED ALLENES,SULFENYL CHLORIDES,1,2-OXAPHOSPHOL-3-ENE DERIVATIVES,POTASSIUM DICHLOROIODATE(I),INTRAMOLECULAR CYCLIZATION,ELECTROPHILIC CYCLIZATION},
  language     = {eng},
  number       = {69},
  pages        = {17413--17431},
  title        = {Fifty years of (benz)oxaphospholene chemistry},
  url          = {http://dx.doi.org/10.1002/chem.201703129},
  volume       = {23},
  year         = {2017},
}

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