Photochemistry of Bis(diazomethyl)silanes:  A Novel Approach to 1<i>H</i>-Silirenes

Zielinski, Magdalene; Trommer, Martin; Sander, Wolfram

doi:10.1021/om990120j

Cited by 9 publications

(4 citation statements)

References 20 publications

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“…[68] A tendency to isomerize was also demonstrated by the bis(diazirinyl)silane 78a (Scheme 21, IR: 1642, 1639 cm -1 ). [71,72] Short-wavelength irradiation in an Ar matrix gave an insignificant quantity of a diazo compound, most likely 79a, together with the silirene 80a. The IR data, however, do not allow distinction between a mixture of 79a with the bisdiazirine 78a and the diazodiazirine 81a.…”

Section: Silyldiazirinesmentioning

confidence: 99%

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Valence Isomerization between Diazo Compounds and Diazirines

Korneev

2011

Eur J Org Chem

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Diazo compounds and diazirines have been separately studied in detail and are widely used in research and for applied purposes. Although the mutual isomerization of these compounds was discovered 50 years ago, it has still been only modestly investigated. Meanwhile, this type of mutual transformation has to be taken into account on every occasion when one of these compounds is used or investigated. This review discusses all main cases of mutual isomerization between diazo compounds and diazirines with the goal of providing an impulse for its rational application, as well as describing the isomerism.

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Section: Silyldiazirinesmentioning

confidence: 99%

“…[71,72] Short-wavelength irradiation of 79a-c (305 nm) rapidly resulted in the disappearance of the diazo compounds and the silirenes 80a-c were the only products.…”

Section: Diazomethanesmentioning

confidence: 99%

Valence Isomerization between Diazo Compounds and Diazirines

Korneev

2011

Eur J Org Chem

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“…Bis(diazomethyl)silanes provide convenient starting materials for a range of silirenes. 41 The general chemistry is given in Scheme 1. This provides an alternative unimolecular route to silirenes-previous methods had typically depended upon the bimolecular reaction of a silylene with an alkyne.…”

Section: Main Group Compoundsmentioning

confidence: 99%

2 Matrix isolation

Almond

Wiltshire

2001

Annu. Rep. Prog. Chem., Sect. C

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“…The products were characterised by IR and the results compared to predictions based on calculations. 209 The stable cationic silane 118 can be used as a Lewis acid catalyst for Diels^Alder reactions. Although the enantiomeric excesses (e.e.…”

Section: Scheme 19mentioning

confidence: 99%

5 Carbon, silicon, germanium, tin and lead

Parr

2000

Annu. Rep. Prog. Chem., Sect. A

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A number of review articles relevant to this chapter have appeared. The area of carbon-rich ligands has been the subject of two timely publications, a special issue of the Journal of Organometallic Chemistry 1 on carbon-rich organometallic complexes and a complementary review on cumulenylidenes. 2 The catalytic applications of metal vinylidenes 3 and the occurrence of planar carbon in organometallic complexes of group 4 and 5 elements 4 have also been reviewed. For silicon, reviews have been in the area of the formation of monolayers 5 and the chemical processing of silicon wafers. 6 A review discussing the role of p-block elements, largely tin, in determining the structure of heterometallic complexes has been published. 7 Despite the discovery of fullerenes, the newest allotrope of carbon, much interest remains in one of the older examples, diamond. The reaction of carbon tetrachloride with four equivalents of sodium metal at 973 K in the presence of a Co/Ni catalyst yields C dia . The product, identi¢ed by Raman spectroscopy, is formed as a powder in a low (ca. 2%) yield, but nevertheless this is amongst the lowest energy routes to industrial diamonds yet known. 8 The same product can be prepared using conditions designed to mimic those found on Uranus and Neptune in which methane is heated to (2^3) Â 10 3 K at pressures of 10^50 gigapascals, whereupon the methane breaks down to form diamond and polymeric hydrocarbons. 9 A convincing argument has been presented for the formation of such a dense solid from a light gaseous phase contributing to the internal heat, magnetic ¢eld and luminosity of a celestial body, and hence the possible signi¢cance of this process in planet formation. A report of the synthesis and identi¢cation of C 6 CH 2 as :C( C C) 2 C CH 2 by removal of the charge from the C 6 CH 2 À. radical anion during neutralisationreionisation mass spectroscopy has been published and related to the cumulenes found in circumstellar dust. 10 Cumulene complexes of transition metals continue to attract much attention. Although synthetic protocols are well established, some new approaches have appeared outlined in Scheme 1. 11,12 The last compound shown is a very rare example of a linear ten atom chain C 8 Rh 2 . Cumulenes with extremely long carbon chains have also appeared, such as 3 which shows in the solid state a distinct twisting of the C 12 chain away from linear, 13 and 4 and 5 (Scheme 2). The crystal structure of 5 shows C^C bond lengths of 1.210^1.233 Ð for triple bonds

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Photochemistry of Bis(diazomethyl)silanes: A Novel Approach to 1H-Silirenes

Cited by 9 publications

References 20 publications

Valence Isomerization between Diazo Compounds and Diazirines

Valence Isomerization between Diazo Compounds and Diazirines

2 Matrix isolation

5 Carbon, silicon, germanium, tin and lead

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