Reactions of 2,3-dihydro-2-phenyliodonium-3-oxo-benzo[b] thiolenide-1,1-dioxide

Hadjiarapoglou, Lazaros P.; Schank, Kurt

doi:10.1016/s0040-4039(00)70647-2

Cited by 28 publications

(9 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…R f = 0.23 (40% EtOAc/hexanes, UV active); m.p. : 102−103 °C; IR (ATR): 2970,2930,1736,1636,1612,1467,1347, 1187 cm −1 ; 1 H (500 MHz, CDCl 3 ) δ 0.85 (t, J = 7.2 Hz, 3H), 1.18 (s, 3H), 1.23 (s, 3H), 2.33 (s, 2H), 2.43 (d, J AB = 17.7 Hz, 1H), 2.50 (d, J AB = 17.7 Hz, 1H), 3.21 (s, 3H), 3.84 (q, J = 7.2 Hz, 2H), 4.26 (s, 1H), 6.84 (d,J = 7.9 Hz,1H),7.04 (dd,J = 7.6,7.6 Hz,1H),7.27 (d,J = 6.8 Hz,1H),7.37 (dd,J = 7.8,7.8 Hz, 1H); 13 C{ 1 H} (125 MHz, CDCl 3 ) δ 13. 6, 26.5, 27.9, 28.9, 34.6, 37.6, 50.8, 52.5, 61.1, 87.8, 108.6, 111.8, 123.1, 123.8, 125.6, 131.4, 144.1, 168.3, 173.2, 177.1, 193.2 3h.…”

mentioning

confidence: 99%

Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles

2017

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles

2017

View full text Add to dashboard Cite

show abstract

“…Following our studies directed towards the development of new synthetic applications of iodonium ylides 6 , we thought that heavily substituted dihydrofurans could be easily obtained by the reaction of a b-dicarbonyl iodonium ylide and a conjugated diene. The use of 1,3-diene has been emerging from the point of view that an extra double bond moiety in the dihydrofuran could lead to further interesting transformations, as well as that the presence of this extra olefinic moiety should influence the behaviour of the reacting double bond.…”

mentioning

confidence: 99%

Cycloaddition Reactions of Iodonium Ylides of Cyclic β-Diketones with 1,3-Dienes: Evidence for a Stepwise Mechanism

Alexiou¹,

Gogonas²,

Hadjiarapoglou³

1999

Synlett

View full text Add to dashboard Cite

The irradiation of a cyclic b-dicarbonyl iodonium ylide with 1,3-diene in acetonitrile gives substituted dihydrofurans in moderate to high yields, presumably via a stepwise mechanism.Iodonium ylides 1 are considered as synthetic equivalents of the corresponding diazo compounds, without major drawbacks such as explosion, toxicity, and/or carcinogenicity. Furthermore, b-dicarbonyl and b-disulfonyl iodonium ylides are readily prepared 2,3 in high yields from the related active methylene compounds and a hypervalent iodine precursor. The photochemical and/or metal-catalyzed decomposition of these stable iodonium ylides generated reactive intermediates, which undergo several types of reactions, i.e. transylidation 1 with various nucleophiles, cycloaddition reactions leading either to the formation of cyclopropanes 3,4 or five-membered heterocycles 5 , etc.Following our studies directed towards the development of new synthetic applications of iodonium ylides 6 , we thought that heavily substituted dihydrofurans could be easily obtained by the reaction of a b-dicarbonyl iodonium ylide and a conjugated diene. The use of 1,3-diene has been emerging from the point of view that an extra double bond moiety in the dihydrofuran could lead to further interesting transformations, as well as that the presence of this extra olefinic moiety should influence the behaviour of the reacting double bond. We have previously published 6a,d the synthesis of dihydrofurans starting from iodonium ylide 1a and alkenes. Based on these results, we now wish to report the synthesis of 1,5-dienes 3 by the reaction of iodonium ylides 1a,b with 1,3-dienes 2.Irradiation of a suspension of iodonium ylide 1a, and 1,3-diene 2a in CH 3 CN for 60 min at room temperature afforded 7 dihydrofuran 8 3a in 83% yield (Scheme 1). The reaction was extended to iodonium ylide 1b and a variety of 1,3-dienes 2b-f, which underwent facile cycloadditions, affording the related dihydrofurans 3 in moderate to excellent yields (Table). When the reactions were repeated thermally, in the presence of catalytic amounts of Cu(acac) 2 , complex mixtures of inseparable products were isolated instead.It is noteworthy that the reaction proceeds without the use of an inert atmosphere. Acyclic 2a-d, with varied degree Scheme 1Downloaded by: University of Arizona Library. Copyrighted material.

show abstract

“…Óτéò äυο τåëåυτáßåò äåêáåτßåò υπÜñ÷åé óηìáíτéêÞ åñåυíητéêÞ äñáóτηñéüτητá óτο πåäßο τηò ÷ηìåßáò του υπåñóθåíούò éωäßου. [1][2][3][4][5][6][7] Ôο éþäéο Ý÷åé τη ìåãáëύτåñη áτοìéêÞ áêτßíá êáé åßíáé το ëéãüτåñο ηëåêτñáñíητéêü áπü τá áëοãüíá. ¸÷åé, åπßóηò, τηí éêáíüτητá ó÷ηìáτéóìού ποëëþí äåóìþí óυíáñìοãÞò, êυñßωò ìå ηëåêτñáñíητéêÜ óτοé÷åßá Þ οìÜäåò.…”

Section: éóτïñιêþ áíαδñïìþunclassified

“…Ôá éωäο υëßäéá τωí â-äéêáñâοíυëéêþí åíþóåωí áποτåëούí τυπéêÞ πηãÞ 1,3-äéπüëωí, áíτéäñούí ìå äéÜöοñåò áêüñåóτåò åíþóåéò êáé äßíουí πñοúüíτá êυêëοπñοóθÞêηò ìå óύã÷ñοíη áπüóπáóη éωäοâåíaeοëßου. [5][6][7]21,33,62,[77][78][79][80][81] Åπßóηò, áíτéäñούí ìå äéÜöοñá äéποëáñüöéëá, üπωò äéθåéÜíθñáêá, íéτñßëéá, θåéοâåíaeοöáéíüíåò êáé êåτÝíåò êáé οäηãούí óå åτåñοêυêëéêÜ πñοúüíτá. Ïé áíτéäñÜóåéò êυêëοπñοóθÞêηò τωí éωäο υëéäßωí áπáéτούí τη ÷ñÞóη êáτáëυτéêÞò ποóüτητáò áëÜτωí ÷áëêού Þ ñοäßου, áí êáé ο áêñéâÞò ìη÷áíéóìüò τηò äéáäéêáóßáò äåí åßíáé áêüìη îåêÜθáñοò.…”

Section: áíτιδñüóåιò êυêëïπñïóθþêηòunclassified

Αντιδράσεις Των Ιωδο Υλιδίων Β-Δισουλφονών Και Β-Δικετονών

Νυχάς¹

View full text Add to dashboard Cite

ÐÅÑÉÅ×ÏÌÅÍÁ ÅÉÓÁÃÙÃÇ 1. Õëßäéá του Ιωäßου 1.1 ΙóτοñéêÞ áíáäñοìÞ 1.2 ÃåíéêÞ äοìÞ τωí υëéäßωí του éωäßου 1.3 ΠáñáóêåυÞ τωí éωäο υëéäßωí êáé áποóύíθåóη 1.4 ÁíτéäñÜóåéò τωí éωäο υëéäßωí 1.4.1 ÁíτéäñÜóåéò ìå ηëåêτñοíéüöéëá áíτéäñáóτÞñéá 1.4.2 ÁíτéäñÜóåéò ÊυêëοπñοóθÞêηò 1.4.3 ÁíτéäñÜóåéò Ôñáíóυëéäßωóηò 1.4.4 Áaeéñéäéíßωóη êáé áìßíωóη 1.5 Ιωäο υëßäéá öáéíοëþí Þ 1,4-äßποëá 1.6 Ιωäο υëßäéá τωí â-äéóουëöοíþí ÁÐÏÔÅËÅÓÌÁÔÁ-ÓÕAEÇÔÇÓÇ 2. Ιωäο υëßäéá â-äéóουëöοíþí 2.1 ΠáñáóêåυÞ éωäο υëéäßωí â-äéóουëöοíþí êáé áποóύíθåóη 2.2 ÁíτéäñÜóåéò éωäο υëéäßωí â-äéóουëöοíþí ìå íοñâοíυëÝíéο êáé éωäοáëêÜíéá 2.3 ×áëêüíåò. Óύíθåóη êáé åöáñìοãÝò 2.4 ÁíτéäñÜóåéò éωäο υëéäßωí â-äéóουëöοíþí ìå ÷áëêüíåò 3. Ιωäο υëßäéá â-äéêáñâοíυëéêþí åíþóåωí 3.1 Óύíθåóη τωí â-äéêáñâοíυëéêþí éωäο υëéäßωí êáé áποóύíθåóη 3.2 ÁíτéäñÜóåéò êυêëοπñοóθÞêηò éωäο υëéäßωí 3.2.1 ÁíτéäñÜóåéò ìå áëêÝíéá 3.2.2 ÁíτéäñÜóåéò ìå áëêßíéá 3.2.3 ÁíτéäñÜóåéò ìå äéÝíéá 3.2.4 ÁíτéäñÜóåéò ìå öουñÜíéá 3.2.5 ÁíτéäñÜóåéò ìå θåéοêáñâοíυëéêÝò åíþóåéò 3.2.6 ÁíτéäñÜóåéò ìå äéöáéíυëο êåτÝíη ÐÅÉÑÁÌÁÔÉÊÏ ÌÅÑÏÓ 4.1 ÓυóêåυÝò-¼ñãáíá 4.2 Óύíθåóη τωí â-äéóουëöοíþí êáé τωí áíτßóτοé÷ωí éωäο υëéäßωí 4.3 ÁíτéäñÜóåéò éωäο υëéäßωí â-äéóουëöοíþí ìå íοñâοíυëÝíéο ii 4.4 ÁíτéäñÜóåéò éωäο υëéäßωí τωí â-äéóουëöοíþí µå áëêυëοúωäßäéá 4.5 Óύíθåóη ×áëêοíþí 4.6 ÁíτéäñÜóåéò éωäο υëéäßωí â-äéóουëöοíþí ìå ÷áëêüíåò 4.7 Óύíθåóη τωí â-äéêáñâοíυëéêþí éωäο υëéäßωí êáé áποóύíθåóη 4.8 ÁíτéäñÜóåéò ìå áëêÝíéá 4.9 ÁíτéäñÜóåéò ìå áëêßíéá 4.10 ÁíτéäñÜóåéò ìå äéÝíéá 4.11 ÁíτéäñÜóåéò ìå öουñÜíéá 4.12 ÁíτéäñÜóåéò ìå θåéοêáñâοíυëéêÝò åíþóåéò 4.13 ÁíτéäñÜóåéò ìå äéöáéíυëο êåτÝíη ÐÅÑÉËÇΨÇ 5. Πåñßëηøη ÂÉÂËÉÏÃÑÁÖÉÁ 6. Âéâëéοãñáößá 141 iii Ðñüëïãïò Ôá υëßäéá του éωäßου áποτåëούí ìéá τÜîη åíþóåωí του υπåñóθåíούò éωäßου, οé οποßåò âñßóêουí ποéêßëåò åöáñìοãÝò óτηí οñãáíéêÞ óύíθåóη. Óêοπüò τηò πáñούóáò åñãáóßáò Þτáí η ìåëÝτη τωí áíτéäñÜóåωí τωí éωäο υëéäßωí τωí â-äéóουëöοíþí, êáθþò êáé τωí êυêëéêþí â-äéêáñâοíυëéêþí éωäο υëéäßωí. ÁíáëυτéêÜ åîåτÜóτηêáí οé áíτéäñÜóåéò τωí éωäο υëéäßωí â-äéóουëöοíþí ìå íοñâοíυëÝíéο, πáñουóßá Þ ìη, áëêυëο éωäéäßωí, êáθþò êáé οé áíτéäñÜóåéò τουò ìå ìéá ποéêéëßá ÷áëêοíþí. ÅîåτÜóτηêáí, åπßóηò, οé áíτéäñÜóåéò τωí éωäο υëéäßωí τηò 1,3êυêëοåîáíοäéüíηò êáé 1,3-êυêëοπåíτáíοäéüíηò ìå πëηθþñá äéποëáñüöéëωí óå äéÜöοñåò óυíθÞêåò áíτßäñáóηò, οé οποßåò Ýäωóáí τá πñοéüíτá êυêëοπñοóθÞêηò ìå ìÝτñéåò åþò êáëÝò áποäüóåéò. Ïé áíτéäñÜóåéò τωí éωäο υëéäßωí τωí â-äéóουëöοíþí ìå áëêυëο éωäßäéá οäÞãηóáí óτá áíτßóτοé÷á áëêυëáëοãοíßäéá êáé óå áëêυëο υποêáτåóτηìÝíåò äéóουëöüíåò. Ïé áíτéäñÜóåéò τωí éωäο υëéäßωí τωí â-äéóουëöοíþí ìå íοñâοíυëÝíéο οäÞãηóáí óτá éíäáíéêÜ πáñÜãωãá, åíþ η áíτßäñáóη ìå íοñâοíυëÝíéο πáñουóßá éωäοìåθáíßου οäÞãηóå óτο πñοúüí ηëåêτñοíéüöéëηò πñοóθÞêηò óτοí äéπëο äåóìü του íοñâοíυëåíßου. Ïé áíτéäñÜóåéò τωí äéò(áñυëοóουëöοíυëο)éωäο υëéäßωí ìå ÷áëêüíåò οäÞãηóáí óå éíäáíéêÜ πáñÜãωãá, óå πñοéüíτá äéÜóπáóηò, πáñåìâοëÞò óτοí οëåöéíéêü C-H äåóìü êáé óå öëáâáíüíåò. Ïé áíτéäñÜóåéò τωí â-äéêáñâοíυëéêþí éωäο υëéäßωí ìå áëêÝíéá, áëêßíéá, äéÝíéá, öουñÜíéá, θåéού÷á äéποëáñüöéëá êáé êåτÝíåò, οäÞãηóáí óτá áíτßóτοé÷á πñοúüíτá êυêëοπñοóθÞêηò, που...

show abstract

Reactions of 2,3-dihydro-2-phenyliodonium-3-oxo-benzo[b] thiolenide-1,1-dioxide

Cited by 28 publications

References 7 publications

Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles

Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles

Cycloaddition Reactions of Iodonium Ylides of Cyclic β-Diketones with 1,3-Dienes: Evidence for a Stepwise Mechanism

Αντιδράσεις Των Ιωδο Υλιδίων Β-Δισουλφονών Και Β-Δικετονών

Contact Info

Product

Resources

About