1833-29-0Relevant academic research and scientific papers
Reactions of 1,2-Oxaphospholenes. 4. Responses toward Oxidations, Cycloadditions, and Conjugate Additions
Macomber, Roger S.,Constantinides, Ioannis,Garrett, Garry
, p. 4711 - 4716 (2007/10/02)
In contrast to the more normal reactivity of the carbon-carbon double bond in vinyl phosphonates, the oxaphospholene double bond in 5,5-dimethyl-2-phenyl-1,2-oxaphosphol-3-ene 2-oxide (7) has proven to be quite resistant to a broad spectrum of reagents in
Sulfur- and Selenium- Promoted Cyclization of Allenic Phosphonates and Phosphinates to Substituted 1,2-Oxaphosphol-3-enes; Stereochemical Consequences at Phosphorus. The Crystal and Molecular Structure of (Z)-3,5-Di-tert-butyl-2-methoxy-4-(phenylseleno)-1,2-oxaphosphol-3-ene 2-Oxide
Macomber, Roger S.,Krudy, George A.,Seff, Karl,Rendon-Diazmiron, L. E.
, p. 1425 - 1430 (2007/10/02)
A series of allenic phosphonate esters (4a-d) and phosphinate 6 were reacted with benzeneselenyl chloride.Except for 4a, which gave a simple 1,2-adduct, each ester afforded the corresponding 4-(phenylseleno)-1,2-oxaphosphol-3-ene (11b-e).Similar reaction of the esters with 2,4-dinitrobenzenesulfenyl chloride gave the corresponding 4-thio derivatives (13) in cases 4c, 4d and 6; 4a and 4b were unreactive.The diastereomers of 11b were seperated, and the structure of the Z isomer was established by X-ray crystallography.The stereochemistry of the cyclization and related reactions is discussed.
