Preparations and Reactions of 10-(Halomethylene)anthrones

Article abstract of DOI:10.1021/jo00357a027

(Halomethylene)anthrones 3 and 4 were prepared by the simple method from 10-methylene- and 10-benzylideneanthrones.The reaction of 3 with azide ion gave 10-(azidomethylene)anthrone 5a, which afforded 16 and/or 17 by photolysis and thermolysis, while similar treatment of 4-led to spiro 19.The reaction of 3 and 4 with cyanide ion gave the corresponding 10-(cyanomethylene)anthrones 5b and 6b. (Halomethylene)anthrone 3 reacted with methoxide ion, hydroxide ion, and aniline to give 5c, 5d and 5e, respectively.