Spiro [4.4] nonatetraene and spiro [4.4] nona-1, 3, 7-triene. Synthesis and properties. Effects of spiroconjugation

MF Semmelhack, JS Foos, S Katz

Index: Semmelhack,M.F. et al. Journal of the American Chemical Society, 1973 , vol. 95, # 22 p. 7325 - 7326

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Citation Number: 75

Abstract

Abstract: Spiro [4.4] nonatetraene (1) was prepared for the first time by a relatively direct synthesis starting from allyl bromide and diethyl malonate. Spiro [4.4] nona-l, 3, 7-triene (2) was obtained by a new route, starting from cyclopentadienide anion and 4, 5-di (bromomethyl)-2, 2-dimethyl-l, 3-dioxolane (16). Comparison of the spectral and chemical properties of 1, 2, and spiro [4.4] nona-l, 3-diene (10) revealed significant effects of ...