Synthese und Carben-Reaktionen von 1,2-Bis(1-diazo-2-oxoalkyl)disilanen

Maas, Gerhard; Fronda, Antonio

doi:10.1016/0022-328x(90)85509-w

Cited by 15 publications

(4 citation statements)

References 24 publications

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“…To the best of our knowledge, the silicon compounds, i.e. 4,8‐disubstituted‐3,7‐dioxa‐2,6‐disilabicyclo[3.3.0]‐octa‐4,8‐dienes, reported by Maas et al, represent the only structurally characterized analogues.…”

Section: Resultsmentioning

confidence: 99%

Reactivity of an N,N‐Chelated Germylene Toward Substituted Alkynes, Alkenes, and Allenes

Böserle

Jambor

Erben

et al. 2018

Zeitschrift anorg allge chemie

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Treatment of N,N-chelated germylene [(iPr) 2 NB(N-2,6-Me 2 C 6 H 3 ) 2 ]Ge (1) with ferrocenyl alkynes containing carbonyl functionalities, FcCϵCC(O)R, resulted in [2+2+2] cyclization and formation of the respective ferrocenylated 3-Fc-4-C(O)R-1,2-digermacyclobut-3-enes 2-4 [R = Me (2), OEt (3) and NMe 2 (4)] bearing intact carbonyl substituents. In contrast, the reaction between 1 and PhC(O) CϵCC(O)Ph led to activation of both CϵC and C=O bonds producing bicyclic compound containing two five-membered 1-germa-2-oxacyclopent-3-ene rings sharing one C-C bond, 4,8-diphenyl-3,7-dioxa-2,6-digermabicyclo[3.3.0]octa-4,8-diene (5). With N-methylmaleimide * Dr. L. Dostál E-Mail: libor.dostal@upce.cz [a] Results and DiscussionFerrocenyl-substituted alkynes, FcCϵCC(O)R (where R = Me, OEt, [45] and NMe 2 ), were chosen as possible reagents to test the reactivity of 1 with alkynes substituted by a carbonyl group. The amide has been newly synthesized and structurally characterized (Figure 1) during this work. The amide crystallizes with two nearly identical molecules in the asymmetric unit. The entire C 5 H 4 CϵCC(O)NMe 2 fragments in both molecules are essentially planar, which maximizes possible conjugation of their π systems.The treatment of germylene 1 [41] with above mentioned alkynes resulted in a smooth [2+2+2] cyclization and formation of the respective 3-Fc-4-C(O)R-1,2-digermacyclobut-3-enes 2-4 [R = Me (2), OEt (3), and NMe 2 (4)] (Scheme 1). No products resulting from an attack of the germylene on the carbonyl moiety could be isolated and the reactivity of 1 thus resembles that described earlier for simple alkynes. [42]

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Section: Resultsmentioning

confidence: 99%

Reactivity of an N,N‐Chelated Germylene Toward Substituted Alkynes, Alkenes, and Allenes

Böserle

Jambor

Erben

et al. 2018

Zeitschrift anorg allge chemie

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“…1-Benzyl-1-methylcyclopropane and all the ketone dimers of anions 1a-e and g-h are well known and exhibited physical properties identical to those reported in the literature. [20][21][22][23][24] Representative experimental procedure. These reactions were carried out in a 10 mL three-necked Schlenk tube, equipped with a nitrogen gas inlet and a magnetic stirrer.…”

Section: Methodsmentioning

confidence: 99%

Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane

2016

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“…Photolysis or catalytic decomposition of bissilanyldiazomethyl ketones 46 lead to the formation of 4,8-disubstituted 3,7-dioxa-2,6-disilabicyclo[3.3.0]-octa-4,8-dienes 47 in 6−26% yields (Scheme ) 10 …”

Section: Heterocycles From Carbenes Bearing One Heteroatom Substituentmentioning

confidence: 99%

“…25 Photolysis or catalytic decomposition of bissilanyldiazomethyl ketones 46 lead to the formation of 4,8disubstituted 3,7-dioxa-2,6-disilabicyclo[3.3.0]-octa-4,8-dienes 47 in 6-26% yields (Scheme 10). 26 A silyl-substituted biscarbene or biscarbenoid was generated from bis(diazocarbonyl)silane 48 in the presence of copper triflate or palladium acetate. It probably exists as a cyclic cumulene triene intermediate 49.…”

Section: Silicon-substituted Carbenesmentioning

confidence: 99%