Reactions of tetramesityldisilene with acid chlorides and ketenes

Fanta, Alan D.; Belzner, Johannes; Powell, Douglas R.; West, Robert

doi:10.1021/om00030a029

Cited by 31 publications

(16 citation statements)

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“…Compound 6 results from the addition of benzaldehyde to Mes2Ge:. From the integration of the 'H NMR spectrum, two molecules of the aldeh de have added to the germylene and, from the H NMR and the mass spectra, the structure can be unequivocally assigned as rruns-2,2-dimesityl-4, .5-diphenyl-2-germa-1,3-dioxolane, 6 . The addition is both regioselective and stereoselective.…”

Section: Resultsmentioning

confidence: 99%

“…The refinements in this space group (Pl) were not processed further due to severe correlations and convergence problems. The problem of twinning (3) 5795 (2) 5748 (3) 4741 (3) 3782 (3) 1284 (3) 1482 (2) 673 ( (7) 234 1 (6) 2326 (5) 61 42 (7) 5009 (6) 2633( 1 ) 2951 (1) 41 68 (5) 4309 (9) 5033 (9) 4872 (9) 3774 (8) 4358( 12) 4895 (13) 5169 (14) 2468 (3) 21 26(3) 21 64 (3) 2545 (4) 2888 (3) 2849 (3) 1606 (2) 497(3) -270 (2) 71 (3) 11 79 (3) 1947 (2) 3063 (3) 2537 (3) 2688 (3) 3363 (4) 3889 (3) 3739 (3) 2332 ( (7) 2630 (7) 3243 (6) 51 (5) -805 (6) 3124 (5) 1766 (6) 3518 (7) 4374 (6) 626 (5) 528 (7) 4004 (6) - (6) 3297 (9) 3479 (6) 1655 (6) 4259 (7) 2824 (7) -979 …”

Section: X-ray Stmcture Determinationsmentioning

confidence: 99%

“…In the final least-squares refinement cycles, the data converged at RI = For the inverted model, the full-matrix leastsquares cycles on F2 converged at R , = 0.0625, wR2 = 0.1691, and GooF = s = 1.056 for 1817 (Fo 3 4dFo)) and 239 parameters, and R1 = 0.1078 and wR2 = 0.198 for all 2974 data. The Flack parameter refined to 0.32 (6). The maximum shift/esd = 0.055 for z of C (3).…”

Section: X-ray Stmcture Determinationsmentioning

confidence: 99%

“…The addition reactions of other classes of carbonyl compounds have been investigated, with tetramesityldisilene being used as a representative disilene. Tetramesityldisilene is unreactive toward most esters but has been found to react with methyl furoate [S], diphenylketene [6], dimethylketene [6], and heptafluorobutyryl chloride [61 to give 2,3-disilaoxetanes as well. With the 1,2-diketone, benzil, disilenes undergo a formal [2 or the aromatic ketone acts as the four-electron component, have also been obtained [9,10].…”

Section: Introductionmentioning

confidence: 99%

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The addition of carbonyl compounds to tetramesitylgermasilene and dimesitylgermylene

Baines¹,

Cooke²,

Vittal³

1994

Heteroatom Chemistry

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Section: Resultsmentioning

confidence: 99%

Section: X-ray Stmcture Determinationsmentioning

confidence: 99%

Section: X-ray Stmcture Determinationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The addition of carbonyl compounds to tetramesitylgermasilene and dimesitylgermylene

Baines¹,

Cooke²,

Vittal³

1994

Heteroatom Chemistry

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“…al. [16] and our group [10b] that disilenes react rather unusually with various haloalkanes, giving several types of products (eqs. 7 and 8).…”

Section: Mechanisms Of Reactions Of Disilenes With Haloalkenesmentioning

confidence: 99%

Comparative chemistry of unsaturated compounds of Group 14 elements

Kira

2000

Pure and Applied Chemistry

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Structures and reactions of a stable dialkylsilylene and various cyclic and acyclic disilenes, which we have recently synthesized, are discussed in detail. The stable silylene was found to be well protected sterically from dimerization but least perturbed electronically as evidenced by UV-vis and NMR spectroscopy. Persilylated acyclic and cyclic disilenes have shown interesting features in the Si=Si bond distances, electronic spectra, and reactions, due to the remarkable electronic and steric effects of trialkylsilyl substituents. Detailed theoretical calculations for the addition of water to disilene has shown that the intramolecular antiaddition pathway is rationalized using the orbital symmetry rule. The reactions of disilenes with haloalkanes were judged to proceed via the rate-determining halogen abstraction of disilenes from haloalkanes. The biradical character of disilenes may be related to the small π bond energy.

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