Synthesis and Electrophilic Cyclization Reactions of Diphenyl 3-Methylpenta-1,2,4-trienyl Phosphine Oxide

Ivanov, Ivaylo K.; Christov, Valerij Ch.

doi:10.1080/00397911.2011.609957

Cited by 7 publications

(4 citation statements)

References 24 publications

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“…A rationale for this reaction based on available literature data [13,14,15,16,17,18,19,20,21,22,23] and on our recent results [51,52,53,54] is depicted in Scheme 5.…”

Section: Resultsmentioning

confidence: 99%

“…In [48,49,50] the respective authors comment that this fact is due to the neighbouring group participation effect of the diphenyl phosphine oxide functionality. In recent papers we have reported the reactions of 1-vinyl- [51] and 3-vinylallenyl [52] phosphine oxides with electrophiles leading to formation of various heterocyclic or highly unsaturated compounds.…”

Section: Introductionmentioning

confidence: 99%

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Bifunctionalized Allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes

2014

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This paper discusses a reaction of phosphorylated α-hydroxyallenes with protected or unprotected hydroxy groups involving 5-endo-trig cyclizations. Various electrophilic reagents such as sulfuryl chloride, bromine, benzenesulfenyl and benzeneselenenyl chlorides have been applied. The paper describes the reaction of 1-hydroxyalkyl-1,2-dienephosphonates with electrophiles that produces 2-methoxy-2-oxo-2,5-dihydro-1,2-oxaphospholes due to the participation of the phosphonate neighbouring group in the cyclization. On the other hand, (1E)-alk-1-en-1-yl phosphine oxides were prepared as mixtures with 2,5-dihydro-1,2-oxaphosphol-2-ium halides in a ratio of about 1:2 by chemo-, regio, and stereoselective electrophilic addition to the C 2 -C 3 -double bond in the allene moiety and subsequent concurrent attack of the external (halide anion) and internal (phosphine oxide group) nucleophiles. The paper proposes a possible mechanism that involves cyclization and additional reactions of the phosphorylated α-hydroxyallenes.

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“…A rationale for this reaction based on available literature data [13,14,15,16,17,18,19,20,21,22,23] and on our recent results [51,52,53,54] is depicted in Scheme 5.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bifunctionalized Allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes

2014

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“…It is necessary to carry out this reaction under argon atmosphere since vinylallenyl phosphine oxides are sensitive to the moisture in air. 37,38 The desired product 3a was obtained in 42% yield (see Table 1, entry 1). When the reaction was carried out at reflux, it was complete within 14 hours and the yield was considerably higher (71%, entry 2).…”

Section: Resultsmentioning

confidence: 99%

“…31 During our previous works concerning electrophilic cyclization reactions of alkatrienyl phosphine oxides, we were able to show that 1-37 and 3-vinylallenyl 38 phosphine oxides are readily accessible by [2,3]-sigmatropic rearrangement of the corresponding 1-and 3-vinylpropargylic phosphinites, formed in the reactions of the corresponding -alkynols with diphenylphosphinous chloride.…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereoselective Diels-Alder reaction of diphenyl 5-methylhexa-1,3,4-trien-3-yl phosphine oxide with N-(4-substituted-phenyl)maleimides and maleic anhydride

Ivanov¹,

Ismailov²,

Christov³

2013

Arkivoc

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Dedicated to Professor Marko Kirilov from Sofia University, Bulgaria on the occasion of his 90 th anniversary Abstract Regio-and stereoselective Diels-Alder reaction of diphenyl 5-methylhexa-1,3,4-trien-3-yl phosphine oxide 1 with N-(4-substituted-phenyl)maleimides or maleic anhydride and the formation of a series of the 5-(diphenylphosphinoyl)-4-isopropylidene-2-(4-substituted-phenyl)-3a,4,7,7a-tetrahydroisoindole-1,3-diones 5a-g and the 5-(diphenylphosphinoyl)-4-isopropylidene-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione 3 respectively is described.

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ChemInform Abstract: Synthesis and Electrophilic Cyclization Reactions of Diphenyl 3‐Methylpenta‐1,2,4‐trienyl Phosphine Oxide.

Ivanov

Christov

2013

ChemInform

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Synthesis and Electrophilic Cyclization Reactions of Diphenyl 3-Methylpenta--1,2,4-trienyl PhosphineOxide. -The title compound (III) is readily prepared via an atom-economical [2,3]-sigmatropic rearrangement of an alkenynyl phosphinite formed in situ by reaction of 3-methylpent-1-en-4-yn-3-ol with diphenylchlorophosphine. Electrophilic cyclization reactions of (III) proceed with the formation of various heterocyclic or highly unsaturated compounds with participation of the allenic and/or 1,3-dienic part of the vinylallenic system and neighboring group participation of phosphoryl and/or vinylic group. -(IVANOV, I. K.; CHRISTOV*, V. C.; Synth. Commun. 43 (2013) 6, 800-809, http://dx.doi.org/10.1080/00397911.2011.609957 ; Dep. Org. Chem. Technol., Fac. Nat. Sci., K. Preslavski Univ., BG-9700 Shumen, Bulg.; Eng.) -H. Toeppel 24-172

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Synthesis and Electrophilic Cyclization Reactions of Diphenyl 3-Methylpenta-1,2,4-trienyl Phosphine Oxide

Cited by 7 publications

References 24 publications

Bifunctionalized Allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes

Bifunctionalized Allenes. Part XV. Synthesis of 2,5-dihydro-1,2-oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes

Regio- and stereoselective Diels-Alder reaction of diphenyl 5-methylhexa-1,3,4-trien-3-yl phosphine oxide with N-(4-substituted-phenyl)maleimides and maleic anhydride

ChemInform Abstract: Synthesis and Electrophilic Cyclization Reactions of Diphenyl 3‐Methylpenta‐1,2,4‐trienyl Phosphine Oxide.

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