Wrapping Phosphorus in Vinyl

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Science  06 Feb 2004:
Vol. 303, Issue 5659, pp. 733
DOI: 10.1126/science.303.5659.733a

The vinyl group, CH2=CHX, has one of the most extensively developed chemistries. However, when X is phosphorus, many simple examples of vinyl compounds are unknown or have not been reproduced synthetically. Monkowius et al. report on the synthesis of the tetra(vinyl)phosphonium cation, [(CH2=CH)4P]+. Synthesis from trivinylphosphine led to unwanted polymerization reactions, so the authors focused on a strategy in which all four vinyl groups were formed in the last step of synthesis. They prepared the 2-acetoxyethyl precursor, [P(CH2CH2OAc)4]+I, which, upon heating in the presence of base, produced the tetravinyl cation. They have used this species as a highly reactive precursor for a number of reactions. — PDS

J. Am. Chem. Soc. 10.1021/ja0399019 (2004).

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