| Autor: |
Harold W. Moore, Walter Weyler, H. Raymond Shelden |
| Jazyk: |
angličtina |
| Rok vydání: |
1969 |
| Předmět: |
|
| Zdroj: |
Moore, HW; Weyler, W; & Shelden, HR. (1969). Rearrangements of azidoquinones VI. Thermal rearrangement of azido-1,4-quinones to 2-cyano-1,3-cyclopentenediones. Tetrahedron Letters, 10(45), 3947-3950. doi: 10.1016/S0040-4039(01)88583-X. UC Irvine: Retrieved from: http://www.escholarship.org/uc/item/0xf4j329 |
| DOI: |
10.1016/S0040-4039(01)88583-X. |
| Popis: |
Tetralledron Letters No.45, pPO 3947-3950, 1969. Pergamon Press. Printed in Great Britain. REARRANGEMENTS OF AZIDGQUINONlB VI. THERMAL REARRANGEMENT OF AZIDO-1, I-QUINONES TO 2-CYANO-1,3-CYCLOPENTENEDIONES Harold W. Moore, Walter Weyler, Jr., and II. Raymond ShelQn Department of Chemistry University of California Irvine, California 92664 (Xeceived in USA 18 July 1969; received in UK for publication 25 August 1969) Previously it was shown that azido-1,4-quinones undergo a highly stereoselective catalyzed ring contraction to y- cyanoalkylidlne- A Q’ ’ - butenoH&s. ’ acid Reported in the present communication is an investigation of the thermal decomposition d selected azido-1,4- quinones ( 1 ), a reaction also resulting in ring contraction giving the 2-cyano-1,3-cyclopen- tenedione ( 3) ring system. This rearrangement provides a new example of a very limited number of known methods in which thermal conversion of a six to a five membered ring can be accomplished. The general structures ( 1) and ( 3) illustrate the overall chemical transformation as indicated by the following possible mechanistic scheme (Scheme I). |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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