Reaction Pathways upon Interaction of Allenic Phosphonates with Selenyl Chlorides

Mondeshka, D. M.; Tancheva, C.; Angelov, H. M.

doi:10.1080/03086648708079205

Cited by 2 publications

(2 citation statements)

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“…12,13 Similarly, the reaction of 1,2-allenylic phosphonates, phosphinates, phosphoric acids with RSeCl and RSeBr was also reported to afford 4-selenyl-2,5-dihydro-1,2-oxaphosphole 2-oxides. [14][15][16][17][18][19][20] Furthermore, the selenohydroxylation of 1,2-allenylic sulfoxides with PhSeCl has been reported by this group. 21 Due to the similarity between the phosphine oxides and sulfoxides or sulfones, we show interest in the selenohydroxylation of 1,2-allenylic phosphine oxides.…”

Section: Introductionmentioning

confidence: 88%

Studies on highly regio- and stereoselective selenohydroxylation reaction of 1,2-allenyl phosphine oxides with PhSeCl

Guo

Qiu

et al. 2009

Tetrahedron

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Section: Introductionmentioning

confidence: 88%

Studies on highly regio- and stereoselective selenohydroxylation reaction of 1,2-allenyl phosphine oxides with PhSeCl

Guo

Qiu

et al. 2009

Tetrahedron

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“…Selenylhalides, in contrast to sulfenylchlorides, selectively yielded oxaphospholenes in some cases, but the formation of 1,2‐ and 2,3‐adducts could not always be avoided in minimally substituted allenylphosphonates . Phosphonylated selenophenes and selenium‐containing bicyclic oxaphospholenes were formed as well .…”

Section: Synthetic Routes Towards Oxaphospholenes and Benzoxaphospholmentioning

confidence: 99%

Fifty Years of (Benz)oxaphospholene Chemistry

Berton

Heugebaert

Virieux

et al. 2017

Chemistry A European J

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The first synthesis of benzoxaphospholenes dates back to the 1960s. Since then,t he structuralv ariety of reported (benz)oxaphospholenesh as steadily increased. Organophosphorusc ompounds have caught the interesto fs ynthetic chemists for ac ouple of decades now because of their interesting biological properties. Oxaphospholenes,i n particular,c ould 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 carbonylc ompoundsw ere reaction types that led to the production of the first (benz)oxaphospholenes.When it was discovered that allenylphosphonates could easily be obtainedf rom propargyl alcohols and dialkylh alophosphites, the electrophile-induced cyclization reaction of these allenylphosphonate precursors resulted in ah uge boom in the amounto fr eports on oxaphospholene synthesis. To this day,t his methodi ss till frequently used. Ring-closing metathesis and Horner-Wadsworth-Emmons reactions have also provent heir potentialf or the preparation of oxaphospholenes. In recent years, Pd, Rh and Au-catalysis have made their entry,g enerating (benz)oxaphospholenes from a wide variety of simple substrates. Ac ouple of miscellaneous methods are summarized at the end of the Review.[a] J.

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Reaction Pathways upon Interaction of Allenic Phosphonates with Selenyl Chlorides

Cited by 2 publications

References 0 publications

Studies on highly regio- and stereoselective selenohydroxylation reaction of 1,2-allenyl phosphine oxides with PhSeCl

Studies on highly regio- and stereoselective selenohydroxylation reaction of 1,2-allenyl phosphine oxides with PhSeCl

Fifty Years of (Benz)oxaphospholene Chemistry

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