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• W2106203610 abstract "The frustrated Lewis pair B(C(6)F(5))(3)/P(o-tolyl)(3) (4a) reacts with 4,6-decadiyne to give the trans-1,2-addition product 5. In contrast, the B(C(6)F(5))(3)/P(t)Bu(3) FLP (4b) reacts with this substrate to give the trans-1,4-adduct trans-6. The cumulene trans-6 undergoes trans-/cis-isomerization upon photolysis to give a ca. 1:1 trans-6/cis-6 mixture. The FLP 4b reacts with 2,6-hexadiyne at r.t. to yield a ca. 4:1 mixture of their trans-1,2- and trans-1,4-addition products (7,8). DFT calculations showed that the zwitterionic 1,4-addition products are favored under thermodynamic control. Thermolysis of the kinetic trans-1,2-addition product (7) (80 °C, bromobenzene) does not lead to the thermodynamically favored 1,4-isomer (8), but instead elimination of isobutylene occurs to the formal trans-1,2-adduct (9) of the B(C(6)F(5))(3)/PH(t)Bu(2) pair. Compounds 5, 6, 7, 8, 9 were analyzed by X-ray diffraction." @default.
• W2106203610 created "2016-06-24" @default.
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• W2106203610 date "2012-01-01" @default.
• W2106203610 modified "2023-10-18" @default.
• W2106203610 title "Frustrated Lewis pair addition to conjugated diynes: Formation of zwitterionic 1,2,3-butatriene derivatives" @default.
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• W2106203610 doi "https://doi.org/10.1039/c2dt30321c" @default.
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