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DOI: 10.1055/s-0030-1261210
Photodimerization of Arenediynes
Contributor(s):Timothy M. Swager, Jan M. SchnorrCalifornia State University, Sacramento and University of California, Davis, USA
Syntheses and Reactivity of Naphthalenyl-Substituted Arenediynes
Org. Lett. 2011, 13: 3660-3663
Publication History
Publication Date:
20 September 2011 (online)
Key words
photocyclization - photodimerization - arenediynes
Significance
Cyclic enediynes as well as terminal acyclic enediynes are well known to undergo photochemical C¹-C6 cycloaromatization. The authors explored the reactivity of naphthalenyl-substituted arenediynes (1 and 2). While the methoxy-substituted derivative 2 undergoes a photo-Bergman cyclization upon irradiation at 300 nm, 1 shows no formation of C¹-C6 or C¹-C5 under these conditions. Irradiation of 1 at 350 nm, however, yields a photodimerized product (4).
Comment
The tandem [2+2] photocyclization yields two products in a 4:1 ratio. The structure of the major product (4) was determined by X-ray crystallographic analysis. Based on NMR studies, the authors suggest that the minor product is a diastereomer of 4.