Synthesis, chemistry, and spectroscopic properties of spiro [3.3] hepta-1, 5-diene

LA Hulshof, H Wynberg

Index: Hulshof,L.A.; Wynberg,H. Journal of the American Chemical Society, 1974 , vol. 96, # 7 p. 2191 - 2200

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Citation Number: 10

Abstract

Abstract: Three syntheses of spiro [3.3] hepta-1, 5-diene (1) are described:(a) pyrolysis of spiro [3.3] heptane-2, 6-bis (trimethy1ammonium) hydroxide in a Hofmann elimination,(b) heating the amine oxide 14 of spiro [3.3] heptane-2, 6-bis (dimethylamine)(8), and (c) a Norrish type I1 photochemical reaction of spiro [3.3] heptane-2, 6-bis (aceto-phenone)(15). Optically active Fecht acid (6) has been used for the preparation of racemic spirocycle 1 ...