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The addition of dialkyl-N-chloramines to aliphatic 1,3-dienes1 1,2-dienea1 terminal olefins, and acetylenes in sulfuric acid-acetic ?cid is described. These facile, free-radical chain reactions all involve the addition of an aminium radical &NH+ to a carbon-carbon multiple bond as the key step in the process, which affords 1: 1 adducts in 15438% yield. Since addition, not hydrogen abstraction, is characteristic of aminium radical reactions with these unsaturated hydrocarbons, chloramination provides a useful, direct route to pchloroalkyl-, pchloroalkenyl-, and &chloro&enylaminw in those casea in which nonradicd reactions or the Hofmann-Loeffler chloramine rearrangement do not compete successfully with the free-radical addition. (2) The most descriptive, although not the earliest, account of their work is given in F. Minisoi, R. Galli, and G. Pollina, Chim. Ind. (Milan), 47, 736 (1965). (3) (a) The bulk of the work is reviewed by M. E. Wolff, Chem. Reo., 68, 55 (1963); see also subsequent articles, e.& (b) R. 8. Nesle and M. R. Walsh, J . Am. Chem. SOC., a?, 1255 (1965); ( 0 ) R. 9. Neale, M. R. Walsh, and N. L. Marcus, J . Ora Chem., 80, 3883 (1965); (d) G. Adam and K. Schreiber, Cham. I d . (London), 989 (1965): (e) E. Sohmitr and D. Murawski, Chem.

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High-energy organosilane esters have been prepared from 2-fluoro-2,2-dinitroethanol (ROH, 1) and chlorosilanes in 85-90 % yields for comparison with the analogous reference compound FEFO, the bisformal of 1. Physical properties and multinuclear NMR data, including ^9Si, are reported for (RO),S¡Me4_, (2a-c, x = 2-4) and Me-(RO)2SiOSi(OR)2Me (4), along with calculated heat contents and detonation properties. The noncompressive shock sensitivity of the high density (1.95 g/cm3) ortho ester 2c was tower than that of the common explosive RDX, although the calculated detonation pressures and velocities were comparable. The compressive shock sensitivity of the bisester 2a was very great, however, in contrast to its very tow noncompressive shock and thermal sensitivities. Hydrolytic sensitivities varied from tow (2a) to exceptionally high (2c). The physical and thermochemical properties of trisester 2b closely resembled those of FEFO, except for a significantly higher boiling point in 2b.