Beese, Giovanna

Bures, Edward

Hunt, Ian R.

Keay, Brian A.

Rogers, Christine

Spinazzé, Patrick G.

PRISM: University of Calgary Digital Repository

Access to full text denied by publisher.  Please contact your local library to acquire the following paper:  Citation:  Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O C and [1,4] C O Silyl Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings Edward Bures, Patrick G. Spinazzé, Giovanna Beese, Ian R. Hunt, Christine Rogers, and Brian A. Keay pp 8741 – 8749.  Abstract:  [1,4] O C and [1,4] C O rearrangements are described for a variety of furans and thiophenes. Treatment of 3-((silyloxy)methyl)furans and -thiophenes with n-BuLi in HMPA provided 2-silylated-3-(hydroxymethyl)furans and -thiophenes in good to excellent yields. The reaction was shown by crossover studies to proceed via an intramolecular [1,4] O C silyl migration. Silyl esters of 3-furoic acids also underwent an intramolecular [1,4] O C silyl migration to provide 2-silylated-3-furoic acids in moderate to good yield when treated with a mixture of LDA and HMPA. Finally, the above silyl migrations were shown to be reversible. Treatment of 2-silylated-3-(hydroxymethyl)furans and -thiophenes with NaH in DMF provided 3-((silyloxy)methyl)furans and -thiophenes in excellent yields via a [1,4] C O silyl migration. The [1,4] C O silyl migration was also shown to be an intramolecular process by a crossover study.  Tables:          Schemes:              DOI: 10.1021/jo971097j

English

Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O C and [1,4] C O Sily1 Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings

Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O C and [1,4] C O Sily1 Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings

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