Abstract
We es tab l i shed that adamantane and a lkyladamantanes reac t under mild conditions with chlorosulfonic acid to yield chlor ides . In adamantane f rom one to th ree hydrogen a toms a re replaced by chlorine, while in 1 ,3-d imethyladamantane f rom one to two hydrogen a toms a re rep laced by chlorine, depending on the reac t ion t ime. The r ep l acemen t occu r s s tepwise , which makes it poss ib le to obtain both the in te rmedia te and end chlorinat ion products in good yield. Thus, the addition of adamantane (I) to chlorosulfonic acid, t aken in an 8-10-fold weight e x c e s s re la t ive to (D, followed by holding the reac t ion mix ture at -5~ for t h, gave, a f t e r the usual workup, 1 -ch loroadamantane (II) in 60.7% yield, mp 163-164~ holding the react ion mix tu re for 60 h gave 1 ,3-d ichloroadamantane (III) in 80.7% yield, mp 130-131 ~ while holding the reac t ion mix tu re for 240 h gave 1 ,3 ,5 t r i ch lo roadamantane (IV) in 70% yield, mp 102 ~
Published Version
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