Journal article

Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates

Abstract:: The conversion of vinyl-substituted 6- and 7-membered cyclic carbonates into 8- and 9-membered medium-ring lactones has been achieved in good yield using dimethyltitanocene in toluene at reflux. The reaction proceeds by initial formation of a ketene acetal which undergoes subsequent in situ Claisen rearrangement to provide the corresponding lactones. The preparation of the cyclic carbonates is carried out under basic conditions and hence this methodology complements our existing selenium-based methodology for the synthesis of medium-ring lactones. © 2002 Published by Elsevier Science Ltd.

Publication status:: Published

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APA Style

Anderson, E., Davidson, J., Harrison, J. R., O'Sullivan, P., Burton, J., Collins, I., & Holmes, A. B. (2002). Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates. TETRAHEDRON, 58(10), 1943–1971.

MLA Style

Anderson, E., et al. “Synthesis of Medium-Ring Lactones via Tandem Methylenation/Claisen Rearrangement of Cyclic Carbonates.” TETRAHEDRON, vol. 58, no. 10, 2002, pp. 1943–71.

Chicago Style

Anderson, E, J Davidson, JR Harrison, P O'Sullivan, J Burton, I Collins, and AB Holmes. 2002. “Synthesis of Medium-Ring Lactones via Tandem Methylenation/Claisen Rearrangement of Cyclic Carbonates.” TETRAHEDRON 58 (10): 1943–71.
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Publisher copy:: 10.1016/S0040-4020(02)00049-2

Authors

+ Anderson, E More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Davidson, J More by this author

Role:: Author

+ Harrison, JR More by this author

Role:: Author

+ O'Sullivan, P More by this author

Role:: Author

+ Burton, J More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

More authors...

Journal:: TETRAHEDRON More from this journal
Volume:: 58
Issue:: 10
Pages:: 1943-1971
Publication date:: 2002-03-04
DOI:: 10.1016/S0040-4020(02)00049-2
ISSN:: 0040-4020

Language:: English
Keywords:: Claisen rearrangement

lactone

medium-ring

carbonate

dimethyltitanocene
Pubs id:: pubs:58703
UUID:: uuid:72298cd1-1bd7-4507-a226-776c7c958dcc
Local pid:: pubs:58703
Source identifiers:: 58703
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2002

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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