Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization

Date

2001-01-01

Author

Demir, Ayhan Sıtkı

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The reaction of tetramethyldiamidophosphoric acid chloride with epoxides in the presence of a trace amount of water furnished 1,3-dienes in good yield. The conversion works with open chain and cyclic epoxides. A C-C bond cleavage reaction occurs if the epoxide contains a quaternary carbon. Application of this method to epoxy sterols afforded ring A aromatic steroids in good yield. The aromatization works via dienol-benzene rearrangements and is independent of the C-3 stereochemistry.

Subject Keywords

Epoxides, Dienes, Steroid and sterols, Aromatization

URI

https://hdl.handle.net/11511/57663

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/s0040-4020(00)01002-4

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, “Tetramethyldiamidophosphoric acid chloride mediated epoxide-diene conversion and steroidal aromatization,” TETRAHEDRON, pp. 227–233, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57663.