SYNTHESIS AND <sup>31</sup>P NMR STUDY OF DIHYDRONAPHTHALENO- AND NAPHTHALENO-DERIVATIVES OF PHOSPHOLENE OXIDES

Orton, William L.; Mesch, Keith A.; Quin, Louis D.

doi:10.1080/03086647908077737

Cited by 21 publications

(8 citation statements)

References 11 publications

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“…The solvent was evaporated in vacuo from the combined organic solutions to give a yellow oil. Chromatography (3% methanol in chloroform) followed by Kugelrohr distillation (76-81°C, 0.2 mm) afforded 9.9 g (68%) of 2 as a colorless oil consisting of a 45 : 55 mixture of dia- 16;H,9.39;found,C,62.14;H,4,5,6,7, …”

Section: 3-dimethyl-245677a-hexahydro-l (H)phosphindole 1 -Oximentioning

confidence: 99%

Diketones from ozonolysis of fused 3‐phospholene oxides: Cyclizations to 3‐phosphorinone and to 1,4‐dihydro‐1,4‐azaphosphinine derivatives

Quin

Marsi

1990

Heteroatom Chemistry

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I -= Me or Ph) were prepared and ozonized at -78°C to give diketones in good yield. The intramolecular aldol condensation was performed on certain o f these ketones to give multicyclic 3-phosphorinone derivatives. I n some cases, double-bond rearrangement into the ring-f'usion position was encountered. The I-phenyl derivative in the benzophosphindole series could not be cyclized due to ready displacement of the P fragment from the tetralone system. The diketones reacted with ammonium acetate to give multicyclic derivatives of the 1,4-dihydro-l,4-azaphosphinine ring system. 1,2,3,4,5,6,7,8-0ctahydro-3-oxo-l -phenylphosphinoline I-oxide was used to demonstrate the value o f the bicyclic 3-phosphorinones as precursors of I-phosphadecalone derivatives. The carbonyl group was protected as the ethylene ketal and the double bond (as well as the benzene ring) was hydrogenated with ease. Hydrolysis gave the l-phospha-3decalone derivative. Reduction o f the same 3-phosphorinone with NaBH4 gave a mixture of diastereomeric alcohols.

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Section: 3-dimethyl-245677a-hexahydro-l (H)phosphindole 1 -Oximentioning

confidence: 99%

Diketones from ozonolysis of fused 3‐phospholene oxides: Cyclizations to 3‐phosphorinone and to 1,4‐dihydro‐1,4‐azaphosphinine derivatives

Quin

Marsi

1990

Heteroatom Chemistry

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“…Our 13 C NMR data was in good agreement with the available information. 30 mp 177−178 °C (lit. 30 (racemic)-trans-2-Phenyl-2,3,3a,4,7,7a-hexahydro-1H-isophosphindole 2-Oxide (22).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

“…30 mp 177−178 °C (lit. 30 (racemic)-trans-2-Phenyl-2,3,3a,4,7,7a-hexahydro-1H-isophosphindole 2-Oxide (22). This was prepared according to General Procedure B using a solution of POPhCl 2 (97.5 mg, 0.50 mmol) in THF (3.20 mL) and a solution of di-Grignard reagent 16 (0.13 M in THF, 3.85 mL, 0.50 mmol).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

“…Flash chromatography (100% EtOAc to 2% NEt 3 /EtOAc) gave 29 (78.9 mg, 72%) as an off-white solid. mp 133−134 °C; TLC (2% NEt 3 /EtOAc) R f = 0.15; 1 H NMR (500 MHz, CDCl (racemic)-1-Allyl-2,3-dihydro-1H-benzo[g]phosphindole-1-oxide (30). This was prepared according to General Procedure B using a solution of PO(allyl)Cl 2 (79.5 mg, 0.50 mmol) in THF (4.95 mL) and a solution of di-Grignard reagent 15 (0.29 M in THF, 1.72 mL, 0.50 mmol).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

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Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes

et al. 2015

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. (2015). Cyclic phosphine oxides and phosphinamides from digrignard reagents and phosphonic dichlorides: modular access to annulated phospholanes. Journal of Organic Chemistry, 80 (19),[9774][9775][9776][9777][9778][9779][9780] Cyclic phosphine oxides and phosphinamides from di-grignard reagents and phosphonic dichlorides: modular access to annulated phospholanes AbstractThe reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of valueadded, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3-and 3,4-positions of the phospholane ring, and a variety of aliphatic, cyclic and aryl Pelectrophiles are tolerated in reasonable to excellent yields. Corresponding author, *email: keller@uow.edu.au (PAK) Abstract: The reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added,

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“…These facts, along with the elemental analysis, suggested structure (18). The dimer decomposed in a few hours in various solvents, but the structure could be stabilrsed in the form of the adduct* (19) with (CD,),CO. 13C N.m.r. spectra (see Table ) are in agreement with the proposed structures (18) and (19).…”

mentioning

confidence: 99%

Reaction of phospholes with acids; [1,5] proton shifts in 1H-λ⁵-phospholes

Quin¹,

Belmont²,

Mathey³

et al. 1986

J. Chem. Soc., Perkin Trans. 2

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Addition to phospholes of gaseous HCI at -90 "C or of an excess of trifluoromethanesulphonic acid at -70 "C, results in P-protonation. The triflate solutions are stable up to room temperature, but the 1 Hphospholium chlorides form P V adducts at -70 "C, which rapidly rearrange by a [1,5]sigmatropic Hshift. The observed product is a 1 -chloro-2,5-dihydrophospholium chloride. Addition of a chloride ion source to the triflates produces the same result. Unprotonated 3,4-dimethyl-1 -phenyl phosphole was found to react at a double bond of its 1H-phospholium ion, forming a crystalline 1,3'-biphospholium dimer.Considerable evidence has accumulated recently to support the concept that among phosphole derivatives [ 1,5] sigmatropic shifts of P-substituents to a ring a-carbon atom are common. Such rearrangements have been encountered when the phosphorus has co-ordination states of three (H' and phenyl migrations), four (phenyl migration 2), and five (phenyl and alkoxy 4 * 5 migration). Migration appears to be faster for H than for phenyl, with alkoxy slower than either; also Pv derivatives rearrange faster than PIv and PI''. A combination of these two effects suggests that rearrangement should be exceptionally fast when H is a substituent on phosphorus(v), as in a h5-phosphole * This appears to be a new observation for a phosphine salt. Other examples have been encountered in related work and will be reported elsewhere (L. D. Quin and S. E. Belmont).1969, 91, 3308.

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SYNTHESIS AND ³¹P NMR STUDY OF DIHYDRONAPHTHALENO- AND NAPHTHALENO-DERIVATIVES OF PHOSPHOLENE OXIDES

Cited by 21 publications

References 11 publications

Diketones from ozonolysis of fused 3‐phospholene oxides: Cyclizations to 3‐phosphorinone and to 1,4‐dihydro‐1,4‐azaphosphinine derivatives

Diketones from ozonolysis of fused 3‐phospholene oxides: Cyclizations to 3‐phosphorinone and to 1,4‐dihydro‐1,4‐azaphosphinine derivatives

Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes

Reaction of phospholes with acids; [1,5] proton shifts in 1H-λ⁵-phospholes

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SYNTHESIS AND 31P NMR STUDY OF DIHYDRONAPHTHALENO- AND NAPHTHALENO-DERIVATIVES OF PHOSPHOLENE OXIDES

Cited by 21 publications

References 11 publications

Diketones from ozonolysis of fused 3‐phospholene oxides: Cyclizations to 3‐phosphorinone and to 1,4‐dihydro‐1,4‐azaphosphinine derivatives

Diketones from ozonolysis of fused 3‐phospholene oxides: Cyclizations to 3‐phosphorinone and to 1,4‐dihydro‐1,4‐azaphosphinine derivatives

Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes

Reaction of phospholes with acids; [1,5] proton shifts in 1H-λ5-phospholes

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SYNTHESIS AND ³¹P NMR STUDY OF DIHYDRONAPHTHALENO- AND NAPHTHALENO-DERIVATIVES OF PHOSPHOLENE OXIDES

Reaction of phospholes with acids; [1,5] proton shifts in 1H-λ⁵-phospholes