Reactions of trimethylsilyl azide with aldehydes: facile and convenient syntheses of diazides, tetrazoles, and nitriles

Nishiyama, Kozaburo; Oba, Makoto; Watanabe, Akio

doi:10.1016/s0040-4020(01)90003-1

Cited by 80 publications

(37 citation statements)

References 19 publications

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“…Although two-photon absorption cross-section of TMSAz was not reported in the literature, two-photon absorption of TMSAz took place efficiently under the present experimental conditions to produce reactive species such as nitrene, which subsequently reacted with Fe(CO) 5 to form photochemical species having silaimine, isocyanate, and siloxane structures (Birkofer el al. 1967;MacMillan and Washburne 1973;Groutas and Felker 1980;Parker and Sommer 1976a,b;Vorbruggen and Krolikiewicz 1979;Nishiyama and Watanabe 1984;Nishiyama et al 1987).…”

Section: Magnetic Aerosol Particle Formation Under Light Irradiation mentioning

confidence: 99%

“…1967;Parker and Sommer 1976a,b;Vorbruggen and Krolikiewicz 1979;Nishiyama and Watanabe 1984;Nishiyama et al 1987). During the growth reactions of aerosol particles following reactions (3) and (4), photochemical species having silaimine, isocyanate, and siloxane structures may be formed around Fe-Fe core structure.…”

Section: Magnetic Aerosol Particle Formation Under Light Irradiation mentioning

confidence: 99%

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Magnetic Field Effect on Chemical Compositions of Magnetic Aerosol Particles Synthesized Photochemically from a Gaseous Mixture of Iron Pentacarbonyl and Trimethylsilyl Azide

Morita

Okano

Šubrt

2013

Aerosol Science and Technology

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Under intense UV light irradiation with an Nd:YAG laser at 355 nm, a gaseous mixture of iron pentacarbonyl (Fe(CO) 5 ) and trimethylsilyl azide (TMSAz) produced aerosol magnetic particles with diameters of 50-100 nm. Two photon absorption of TMSAz and Fe(CO) 5 took place efficiently to produce trimethylsilyl nitrene and iron carbonyls (Fe(CO) n n = 1-4). In cases where a partial pressure of TMSAz was high, nucleation reactions of aerosol particles proceeded via chemical reactions between trimethylsilyl nitrene and two iron carbonyls, resulting in bridging between two iron carbonyls by silyl nitrene. In cases where a partial pressure of TMSAz was low, the nucleation reactions proceeded via chemical reactions between two iron carbonyls, resulting in the formation of di-iron carbonyls with bridging >C O group. Both of these nucleation reactions took place concurrently during aerosol particle formation. From FT-IR spectral change of sedimentary particles produced under an external magnetic field of up to 5 T, it was found that application of an external magnetic field accelerated the latter chemical reaction to result in the appearance of bridging ν(>C O) band in FT-IR spectrum of the magnetic particles.

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Section: Magnetic Aerosol Particle Formation Under Light Irradiation mentioning

confidence: 99%

Section: Magnetic Aerosol Particle Formation Under Light Irradiation mentioning

confidence: 99%

Magnetic Field Effect on Chemical Compositions of Magnetic Aerosol Particles Synthesized Photochemically from a Gaseous Mixture of Iron Pentacarbonyl and Trimethylsilyl Azide

Morita

Okano

Šubrt

2013

Aerosol Science and Technology

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“…[7] During this process, small amounts of benzylic azide 7 were observed. Although path A via intermediate 8 is possible, [10] we consider that the transformation is more likely to occur through path B, because 8 was not detected during this transformation and the result of Equation (3) is also unreasonable. Interestingly, 7 a was cleanly converted to 2 a [Eq.…”

mentioning

confidence: 99%

Direct Transformation of Methyl Arenes to Aryl Nitriles at Room Temperature

2009

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“…87 The products (1 Z ,3 E ) -99 and (1 E ,3 Z ) -99 were expected due to the stereochemical results of other rearrangement reactions of but -3 -yne -1,2 -diyl precursors. 90 Since vinyl azides bearing acidic allyl protons can be isomerized prototropically (see, for example, 56 → 57 , Scheme 5.9 ), it is not surprising that base -induced rearrangement was also utilized to prepare vinylic azido compounds 106 from allyl azides 105 (Table 5.1 ). 89 Thus, hydrogen cyanide and the nitrile 100 were obtained from rac -97 .…”

Section: New Methods To Prepare Vinyl Azidesmentioning

confidence: 99%