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Synfacts 2011(10): 1077-1077  
DOI: 10.1055/s-0030-1261210
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Photodimerization of Arenediynes

Contributor(s): Timothy M. Swager, Jan M. Schnorr
N. V. Korovina, M. L. Chang, T. T. Nguyen, R. Fernandez, H. J. Walker, M. M. Olmstead, B. F. Gherman, J. D. Spence*
California State University, Sacramento and University of California, Davis, USA
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Publication History

Publication Date:
20 September 2011 (online)

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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).