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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 8
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Original Articles

New Phosphono Substituted 3- and 5-Membered Rings Starting from 3(2-Thienyl)acrylonitriles and α-Phosphoryl Carbanions

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Pages 1341-1357 | Received 15 Jun 2002, Published online: 15 Aug 2006

References

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