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Octacarbonyldicobalt-Induced (1,3) H Shifts in 1-Methylallenecarboxylates and Allenic Lactones


Trifonov, Latchezar S; Orahovats, Alexander S; Heimgartner, Heinz (1987). Octacarbonyldicobalt-Induced (1,3) H Shifts in 1-Methylallenecarboxylates and Allenic Lactones. Helvetica Chimica Acta, 70:1070-1075.

Abstract

The allenecarboxylates 1a, b and allenic lactones 4a, b undergo thermally induced (1,3) H shifts in the presence of Co2(CO)8. The non-isolated 1,3-dienes 2a,b react further affording the Diels-Alder adducts 3a, b (Scheme 1) in high yields. These adducts were not formed in the case of the 2-vinylbutenolides 5a, b (Scheme 2). On irradiation in the presence of Co2(CO)8 or Mn2(CO)10, the studied allenes reacted in a different manner, yielding either cyclization products 7 and 8 (Scheme 3) or products 9 and 10, formed via H abstraction and solvent addition (Schemes 4 and 5).

The allenecarboxylates 1a, b and allenic lactones 4a, b undergo thermally induced (1,3) H shifts in the presence of Co2(CO)8. The non-isolated 1,3-dienes 2a,b react further affording the Diels-Alder adducts 3a, b (Scheme 1) in high yields. These adducts were not formed in the case of the 2-vinylbutenolides 5a, b (Scheme 2). On irradiation in the presence of Co2(CO)8 or Mn2(CO)10, the studied allenes reacted in a different manner, yielding either cyclization products 7 and 8 (Scheme 3) or products 9 and 10, formed via H abstraction and solvent addition (Schemes 4 and 5).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1987
Deposited On:21 May 2014 14:44
Last Modified:05 Apr 2016 17:52
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:F. Hoffmann-La Roche & Co. AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19870700419
Permanent URL: https://doi.org/10.5167/uzh-95993

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