2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES

Mitzel NW, BISSINGER P, RIEDE J, DREIHAUPL KH, SCHMIDBAUR H (1993)
ORGANOMETALLICS 12(2): 413-416.

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Abstract
The reactions of 1,2-bis(bromosilyl)ethane and 1,3-bis(bromosilyl)propane with anhydrous hydrazine lead to the two bicyclic silylhydrazines 1,6-diaza-2,5,7,10-tetrasila[4.4.0]bicyclodecane (1) and bis(1-aza-2,6-disila-1-cyclohexyl) (2), respectively. For compound 1, a distillable liquid with mp 7-degrees-C, the low-temperature crystal structure determination has shown a bicyclic configuration with the N-N unit shared by two slightly twisted, chair-formed heterocycles. The N-NSi2 Units are virtually planar but not orthogonal relative to each other owing to conformational restraints. In crystals of compound 2, mp 57-degrees-C, two six-membered rings each in a half-chair conformation are linked solely through the hydrazine N- N bond. The two planar NNSi2 units are at right angles as expected for a nonforced tetrasilylhydrazine geometry. The N-N bond is longer in 1 than in 2. Variable-temperature H-1 C-13 N-15, and Si-29 NMR spectra of both hydrazines have been measured, and the barrier of ring inversion of 1 has been determined.
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Mitzel NW, BISSINGER P, RIEDE J, DREIHAUPL KH, SCHMIDBAUR H. 2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES. ORGANOMETALLICS. 1993;12(2):413-416.
Mitzel, N. W., BISSINGER, P., RIEDE, J., DREIHAUPL, K. H., & SCHMIDBAUR, H. (1993). 2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES. ORGANOMETALLICS, 12(2), 413-416.
Mitzel, N. W., BISSINGER, P., RIEDE, J., DREIHAUPL, K. H., and SCHMIDBAUR, H. (1993). 2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES. ORGANOMETALLICS 12, 413-416.
Mitzel, N.W., et al., 1993. 2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES. ORGANOMETALLICS, 12(2), p 413-416.
N.W. Mitzel, et al., “2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES”, ORGANOMETALLICS, vol. 12, 1993, pp. 413-416.
Mitzel, N.W., BISSINGER, P., RIEDE, J., DREIHAUPL, K.H., SCHMIDBAUR, H.: 2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES. ORGANOMETALLICS. 12, 413-416 (1993).
Mitzel, Norbert W., BISSINGER, P, RIEDE, J, DREIHAUPL, KH, and SCHMIDBAUR, H. “2 DIFFERENT CYCLIZATION MODES IN THE FORMATION OF SILYLHYDRAZINES”. ORGANOMETALLICS 12.2 (1993): 413-416.
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