A NOVEL N-CH2-N BRIDGING REACTION

Treatment of the methyl iodide salts (4 and 10) of the bridgehead hydrazines, 2-p-anisy 1-1,6-diazabicyclo-[4.3.0]nonane (3) and 2-p-anisyl-1,6-diazabicyclo[4.4.0]decane (9), with refluxing sodium methoxide-methanol resulted in the formation of the N-CH2-N bridged derivatives 2-p-anisyl-1,6-diaza[4.3.1]decane (12) and 2-p-anisyl-1,6-diaza[4.4.1]undecane (14). The same hydrazine salts when treated with sodium-ammonia gave the medium-sized ring compounds 6-p-anisyl-1-methyl-1,5-diazacyclononane (13) and 5-p-anisyl-1-methyl-1,6-diazacyclodecane (15). The formation of the NCH2N derivatives is postulated to occur by a 1,2 shift (17) analogous to a Stevens rearrangement. © 1969, American Chemical Society. All rights reserved.