Synthesis of dihydrophosphorins by the thermal transformation of phosphole-dichlorocarbene adducts

Keglevich, György; Androsits, B.; Tőke, Lásʐló

doi:10.1021/jo00252a043

Cited by 49 publications

(30 citation statements)

References 1 publication

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“…All new products (3, 5, 7, 9, and 10) were characterized by 31 P, 13 C, and 1 H NMR, as well as, mass spectral data.…”

Section: Resultsmentioning

confidence: 99%

“…The 31 P, 13 C, and 1 H NMR spectra were obtained on a Bruker DRX-500 spectrometer operating at 202.4, 125.7, and 500 MHz, respectively. Chemical shifts are downfield relative to 85% H 3 PO 4 or TMS.…”

Section: Methodsmentioning

confidence: 99%

“…1,2-Dihydrophosphinine oxide 8 was synthesized as described earlier [13]. • C in a CEM Discovery microwave reactor (applying maximum of 30 W) for 1 h. The product was recrystallized from hexane/ether (6:1) to give 0.10 g (72%) of product 2; 31 P NMR (CDCl 3 ) δ 37.6 (δ lit 37.0) [3].…”

Section: Methodsmentioning

confidence: 99%

“…31 P NMR (CDCl 3 ) δ 36.8 (36%); 13 -3-on-1-yl)-1,3,2 5-methyl-1-phenyl-1,2,3,6Tetrahydrophosphinine 1-Oxide (9) To 0.20 g (1.01 mmol) of the dibenzooxaphosphorine oxide 1 in 10 mL of dry chloroform, 0.50 mL (1.01 mmol) of 2 M trimethylaluminum in hexane at 0…”

Section: Minormentioning

confidence: 99%

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Phospha‐michael reactions involving p‐heterocyclic nucleophiles

Keglevich

Sipos

Takács

et al. 2008

Heteroatom Chemistry

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P-heterocyclic γ-ketophosphonateswere synthesized by the Michael reaction of methyl vinyl ketone with dibenzo-1,2-oxaphosphorine 2-oxide, 1,3,2-dioxaphosphorine 2-oxide and benzo-1,3,2-dioxaphospholane 2-oxide, respectively. In the first two cases, 50% of 1,8-diazabicyclo[5.4.0]undec-7-ene had to be used that was also required in the addition of dibenzooxaphosphorine oxide to cyclohexenone to result in the formation of the corresponding γ-ketophosphonate. The addition of dibenzooxaphosphorine oxide to less reactive 1,2-dihydrophosphinine oxide was accomplished after activation by an equimolar amount of trimethylaluminum to afford a 3-P(O)<-1,2,3,6-tetrahydrophosphinine oxide, which was subjected to catalytic hydrogenation to provide the corresponding 1,2,3,4,5,6-hexahydrophosphinine oxide.

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“…All new products (3, 5, 7, 9, and 10) were characterized by 31 P, 13 C, and 1 H NMR, as well as, mass spectral data.…”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Minormentioning

confidence: 99%

See 2 more Smart Citations

Phospha‐michael reactions involving p‐heterocyclic nucleophiles

Keglevich

Sipos

Takács

et al. 2008

Heteroatom Chemistry

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“…ring opening of 3-phosphabicyclo[3.1.0]hexane 3-oxide (1), was used as the starting material (Scheme 1) [10][11][12].…”

Section: Resultsmentioning

confidence: 99%

Unexpected condensation reaction of two units of 1,2‐dihydrophosphinine 1‐oxides in the presence of tetracyanoethylene

Keglevich

Kovács

Szöllősy

et al. 2003

Heteroatom Chemistry

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An Elegant Microwave Assisted One‐Pot Synthesis of Di(α‐aminophosphonate) Pesticides

Reddy

Chinthaparthi

Reddy

et al. 2014

Archiv der Pharmazie

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A new class of di(α-aminophosphonate) pesticides were prepared by the Kabachnik-Fields reaction under solvent- and catalyst-free conditions with microwave irradiation, and the products were obtained in good-to-excellent yields at shorter reaction time. These compounds were characterized by IR, (1)H, (13)C, (31)P NMR, and mass spectral data. Among them, compounds 4f, 4c, and 4h showed good pesticidal activity against Spodoptera litura, with 92.6, 91.3, and 89.3% mortality.

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Synthesis of dihydrophosphorins by the thermal transformation of phosphole-dichlorocarbene adducts

Cited by 49 publications

References 1 publication

Phospha‐michael reactions involving p‐heterocyclic nucleophiles

Phospha‐michael reactions involving p‐heterocyclic nucleophiles

Unexpected condensation reaction of two units of 1,2‐dihydrophosphinine 1‐oxides in the presence of tetracyanoethylene

An Elegant Microwave Assisted One‐Pot Synthesis of Di(α‐aminophosphonate) Pesticides

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