Allen–Millar–Trippett rearrangement

The Allen–Millar–Trippett rearrangement is a ring expansion reaction in which a cyclic phosphine is transformed into a cyclic phosphine oxide.^[1] This name reaction, first reported in the 1960s by David W. Allen, Ian T. Millar,^[2] and Stuart Trippett,^[3] occurs by alkylation or acylation of the phosphorus, followed by reaction with hydroxide to give a rearranged product. The hydroxide first attacks the phosphonium atom, followed by collapse to the phosphine oxide with one of the groups migrating off of the phosphorus.

References

^ Hassner, Alfred; Stumer, C. (2002). "Allen–Millar–Trippett Phosphonium Rearrangement". Organic Syntheses Based on Name Reactions. Elsevier. p. 5. ISBN 9780080513348.
^ Allen, David W.; Millar, Ian T. (1969). "The alkaline hydrolysis of some cyclic phosphonium salts: ring-opening and ring-expansion reactions". Journal of the Chemical Society C: Organic (2): 252. doi:10.1039/J39690000252.
^ Fishwick, S. E.; Flint, J.; Hawes, W.; Trippett, S. (1967). "Ring expansion in the alkaline hydrolysis of phosphetanium salts". Chemical Communications (21): 1113. doi:10.1039/C19670001113.

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[1] Hassner, Alfred; Stumer, C. (2002). "Allen–Millar–Trippett Phosphonium Rearrangement". Organic Syntheses Based on Name Reactions. Elsevier. p. 5. ISBN 9780080513348.

[2] Allen, David W.; Millar, Ian T. (1969). "The alkaline hydrolysis of some cyclic phosphonium salts: ring-opening and ring-expansion reactions". Journal of the Chemical Society C: Organic (2): 252. doi:10.1039/J39690000252.

[3] Fishwick, S. E.; Flint, J.; Hawes, W.; Trippett, S. (1967). "Ring expansion in the alkaline hydrolysis of phosphetanium salts". Chemical Communications (21): 1113. doi:10.1039/C19670001113.

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