Cycloaddition reactions of heterophospholes

Bansal, R. K.; Gupta, Neelima; Gupta, Nishi

doi:10.1002/hc.20002

Cited by 34 publications

(15 citation statements)

References 71 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The results indicate, that these reactions are usually accompanied by high diastereo-and regioselectivities [62]. The results indicate, that these reactions are usually accompanied by high diastereo-and regioselectivities [62].…”

Section: [2+4] Cycloadditionmentioning

confidence: 75%

“…Cycloaddition reactions including [2+4] cycloadditions given by heterophospholes have been reviewed recently [62]. It has been found that >C=P-moiety in heterophospholes undergoes Diels-Alder (DA) reactions much more readily than the corresponding carbocyclic system.…”

Section: [2+4] Cycloadditionmentioning

confidence: 99%

“…Heterophospholes with high electron-density on phosphorus atom due to +M effect of a nitrogen in the vicinity are reported to undergo oxidative cheletropic [1+4] cycloadditions at the phosphorus atom with electron-deficient heterodienes such as o-quinones, -diketones, -diimines and azodicarboxylic esters to give spirocyclic products [62]. We have investigated the reaction of 2-phosphaindolizines (4, R 1 CO 2 R) with tetrachloro-o-benzoquinone (TCQ) when 1:2 cycloadducts 91 are obtained which have a sixcoordinated phosphorus, as revealed by 31 P NMR ( = -134 to -141).…”

Section: Cheletropic [1+4] Cycloadditionmentioning

confidence: 99%

See 2 more Smart Citations

Recent Advances in the Chemistry of Anellated Azaphospholes

Bansal¹,

Gupta²,

Kumawat

2007

COC

Self Cite

View full text Add to dashboard Cite

Azaphospholes are 6 aromatic heterocycles incorporating at least one 2 , 3 -phosphorus atom and one 3 , 3nitrogen atom. This review covers the synthesis, structural characterization, reactions and theoretical calculations of azaphospholes anellated to a six-or five-membered heterocyclic ring, reported during the last 10-12 years. Three synthetic methods, namely [4+1] cyclocondensation, [3+2] cyclocondensation and 1,5-electrocyclization make a variety of these phosphorus heterocycles available. The aromatic character of these compounds has been confirmed by carrying out density functional theory (DFT) calculations. Mainly 1 H, 13 C and 31 P NMR studies have been employed for the structural characterization. Almost all the functionalities present in the azaphosphole ring have been investigated and electrophilic substitution reactions of the 1-unsubstituted compounds and Diels-Alder reactions as well as 1,2-addition reactions to the >C=P-moiety have been accomplished successfully. The stereo-and regioselectivities observed in the Diels-Alder reactions have been explained on the basis of DFT calculations. Cheletropic cycloadducts formed from [4+1] cycloaddition of o-quinones on the 2 , 3 -P atom have been obtained. A variety of coordination compounds formed bycoordination of the 2 , 3 -P atom have been prepared.

show abstract

Section: [2+4] Cycloadditionmentioning

confidence: 75%

Section: [2+4] Cycloadditionmentioning

confidence: 99%

Section: Cheletropic [1+4] Cycloadditionmentioning

confidence: 99%

See 1 more Smart Citation

Recent Advances in the Chemistry of Anellated Azaphospholes

Bansal¹,

Gupta²,

Kumawat

2007

COC

Self Cite

View full text Add to dashboard Cite

show abstract

“…Cycloaddition reactions of heterophospholes have received a theoretical treatment 846 and these reactions have also been reviewed. 847 Improvements in the synthesis of fused 1,3-azaphospholes via the reactions of N-alkyl-isoquinolinium salts with phosphorus trichloride have been described and their reactivity towards cycloaddition studied. 848 New fused 1,3-azaphospholes derived from N-alkylquinolinium salts, 849 and new 2H-1,2,3-diazaphospholes, 850 have also been reported.…”

Section: Phosphirenes Phospholes and Phosphininesmentioning

confidence: 99%

Phosphines and Related Tervalent Phosphorus Systems

2006

Organophosphorus Chemistry

View full text Add to dashboard Cite

“…The chemistry of related 1, 2, 3‐diazaphospholes and diazaphospholenes has been extensively studied by Schmidpeter , Bansal and others 3,7,8. These compounds are known to take part in cycloaddition reactions 9. Dialkyl‐1 H ‐ and ‐2 H ‐1, 2, 3‐diazaphospholes became available from ketone hydrazones and PCl 3 10–13.…”

Section: Introductionmentioning

confidence: 99%

The Reaction of Cyclohexanone Azine with PCl₃. Synthesis of Annulated Dichlorodiazaphosphole and its Unusual Transannulation

Kornev

Gorak

Lukoyanova

et al. 2012

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

The N,NЈ-annulated dichlorodiazaphosphole 1 was prepared in 55 % yield by the reaction of cyclohexanone azine (c-HA) with two equivalents of PCl 3 in pyridine. Compound 1 revealed one-dimensional chains in crystal with short intermolecular interactions [3.194(1) Å] between phosphorus atoms of adjacent molecules. Treatment of c-HA with MeLi (2 equiv. in Et 2 O) followed by addition of PCl 3 gave 1 in 33 % yield. An amount of c-HA isomerizes in these * Dr. A. N. Kornev Fax: +7-831-4627497 E-Mail: akornev@iomc.ras.ru [a] G. A. Razuvaev 1173conditions to form corresponding hexahydroindazole derivative 3, which further reacts with 1 to give diazaphosphole 5 as transannulation product. Copper monochloride forms an (1:1) adduct with 5, which was characterized by its X-ray crystal structure. Only one equivalent of PCl 3 reacts with c-HA in Et 2 O/Et 3 N mixture to form diazaphospholium chloride 2 and hexahydroindazole 3.

show abstract

Cycloaddition reactions of heterophospholes

Cited by 34 publications

References 71 publications

Recent Advances in the Chemistry of Anellated Azaphospholes

Recent Advances in the Chemistry of Anellated Azaphospholes

Phosphines and Related Tervalent Phosphorus Systems

The Reaction of Cyclohexanone Azine with PCl₃. Synthesis of Annulated Dichlorodiazaphosphole and its Unusual Transannulation

Contact Info

Product

Resources

About

Cycloaddition reactions of heterophospholes

Cited by 34 publications

References 71 publications

Recent Advances in the Chemistry of Anellated Azaphospholes

Recent Advances in the Chemistry of Anellated Azaphospholes

Phosphines and Related Tervalent Phosphorus Systems

The Reaction of Cyclohexanone Azine with PCl3. Synthesis of Annulated Dichlorodiazaphosphole and its Unusual Transannulation

Contact Info

Product

Resources

About

The Reaction of Cyclohexanone Azine with PCl₃. Synthesis of Annulated Dichlorodiazaphosphole and its Unusual Transannulation