Isolation of a Kinetically Stabilized 1,3,6-Triphosphafulvene

Ito, Shigekazu; Sugiyama, Hiroki; Yoshifuji, Masaaki

doi:10.1002/1521-3773(20000804)39:15<2781::aid-anie2781>3.0.co;2-5

Cited by 52 publications

(49 citation statements)

References 8 publications

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“…2,2-Dibromophosphaethene 24 was allowed to react with t-butyllithium at À78°C to give a new 6-p cyclic compound 26 in 59% yield (Scheme 7) [19]. The reaction appears to involve the addition of 25 to two equivalents of phosphaalkyne 1 generated under the reaction conditions [20] forming an intermediate 27.…”

Section: Formation Of 136-triphosphafulvenementioning

confidence: 99%

Syntheses and reactivity of novel unsaturated cyclic compounds containing phosphorus atoms

Yoshifuji

Sugiyama

Ito

2005

Journal of Organometallic Chemistry

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Section: Formation Of 136-triphosphafulvenementioning

confidence: 99%

Syntheses and reactivity of novel unsaturated cyclic compounds containing phosphorus atoms

Yoshifuji

Sugiyama

Ito

2005

Journal of Organometallic Chemistry

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“…We previously succeeded in preparation and isolation of a kinetically stabilized 1,3,6-triphosphafulvene, 5 and recently we have found its unique electrophilic reactivity providing a number of exotic Pheterocyclic compounds. [6][7][8] Now we are interested in the chemistry of 6-phosphafulvene bearing a cyclopentadienyl group and an exo P C double bond, which is one of the typical phosphaalkene with an electronically perturbed P C moiety.…”

Section: Introductionmentioning

confidence: 99%

Study on Synthesis and Structure of Sterically Demanding 6-Phosphafulvenes

Ito

Miyake

Yoshifuji

2009

Phosphorus, Sulfur, and Silicon and the Related Elements

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t-Butylcyclopentadienyllithium was allowed to react with (2,4,6-tri-tbutylphenyl)phosphonous dichloride to afford the corresponding chloro-5-cyclopentadienylchlorophosphine as a mixture of diastereomers, the structure of one of which was determined by X-ray crystallography. The mixture of 5-cyclopentadienylchlorophosphine diastereomers was treated with a base to furnish novel 2-t-butyl-6-(2,4,6-tri-t-butylphenyl)-6-phosphafulvenes, and each geometrical isomer of them was fully characterized by X-ray crystallography. The E/Z ratio of the 6-phosphafulvene obtained was considerably dependent on the diastereomeric ratio of the chlorophosphine precursor.

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“…affording the corresponding 1,3,6-triphosphafulvene. 12 At the same time, we observed formation of a secondary ethynylphosphine 5 as one of the byproducts. We succeeded in isolation, crystallization, and X-ray structural analysis of 5.…”

Section: Resultsmentioning

confidence: 99%