Quantum-chemical investigation of monosubstituted cyclopropanes

Tupitsyn, I. F.; Shibaev, A. Yu.; Puzanov, Yu. V.

doi:10.1007/bf01004508

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2011

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“…The absence of a germylacetylene during the addition of ethoxyacetylene is notable, particularly since formation of an analogous silylacetylene was observed in the reaction between silene 2 and ethoxyacetylene . The conjugate base of ethoxyacetylene is the weakest base/nucleophile of the alkynes investigated . If the addition of the acetylide anion to the germene is the rate-determining step in the chain, one might expect the rate of the chain reaction to be sensitive to the strength of the anion.…”

Section: Discussionmentioning

confidence: 98%

Reactivity of a Germene toward Terminal Alkynes: Competition between Cycloaddition, Ene-Addition, and CH-Insertion

Pavelka

Baines

2011

Organometallics

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A variety of terminal alkynes were added to Mes 2 GedCHCH 2 t-Bu, a naturally polarized germene. Three different modes of reactivity were observed: cycloaddition to give germacyclobutenes, ene-addition to give vinylgermanes, and addition across the acetylenic CÀH bond to give germylacetylenes. Mechanisms for the formation of the products are proposed. The reactivity of the naturally polarized germene toward terminal alkynes is compared to that of the analogous silene.

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Section: Discussionmentioning

confidence: 98%