Disulfur monoxide. Reaction with dienes

Dodson, R. M.; Srinivasan, V. R.; Sharma, Komal; Sauers, Richard F.

doi:10.1021/jo00980a001

Cited by 45 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[1] However, similar methodologies for phosphorus compounds, which play an important role in our daily life, are limited. [1f] Taking advantage of the exceptionally high reactivity of the five-membered cyclic hydrogen phosphonate 1, [2] we found the first successful rhodium-catalyzed hydrophosphorylation of alkynes, which affords high yields of the corresponding (E)-alkenylphosphonates 2 with excellent regio-and stereoselectivities [Eq. [1f] Taking advantage of the exceptionally high reactivity of the five-membered cyclic hydrogen phosphonate 1, [2] we found the first successful rhodium-catalyzed hydrophosphorylation of alkynes, which affords high yields of the corresponding (E)-alkenylphosphonates 2 with excellent regio-and stereoselectivities [Eq.…”

Section: Rhodium-catalyzed Hydrophosphorylation Ofmentioning

confidence: 99%

Solid-State Isomerization of Atropodiastereomers: Effective Diastereoselection through Polymorphic Transformations

et al. 2001

View full text Add to dashboard Cite

The Â re Á se Averbuch, and Jacques Einhorn* Polymorphism is a fascinating phenomenon accompanied by a lot of strange manifestations. [1] It is generally defined as the existence of a given compound in more than one crystalline form. In conformational polymorphs, [2] a given molecular compound adopts different conformations in different polymorphs. But, at a molecular level, conformational changes may involve quite high energy barriers, allowing in some cases the isolation of separate stereoisomers (atropisomers) which do not interconvert rapidly in solution at room temperature, but do so if enough energy is supplied. Herein we report solid-state thermal isomerizations of compounds 1, which present such a type of atropisomerism. These isomerizations have features reminiscent of polymorphic transformations, although not involving polymorphs in the usual sense of the word. [3] As depicted in Scheme 1, the synthesis of 1 has been achieved by Diels ± Alder reactions between isobenzofuran 2 and maleimide or N-benzylmaleimide, giving adducts 3 a or 3 b in good yields. Their aromatization under strongly acidic conditions furnished 1 a and 1 b quantitatively. Demethylation of 1 a and 1 b gave diphenols 1 c and 1 d in high yields. Scheme 1. Reagents, conditions, and yields: a) for 3 a: 1 equiv maleimide, toluene, RT, 6 h, 96 %; for 3 b: 1 equiv N-benzylmaleimide, toluene, RT, 6 h, 81 %; b) 6 equiv MeSO 3 H, CH 2 Cl 2 , RT, 12 h, b 99 % for 1 a, b 99 % for 1 b; c) 3 equiv BBr 3 , CH 2 Cl 2 , À 78 8C to RT, 15 h, 98 % for 1 c, 99 % for 1 d. Full details can be found in the Supporting Information. RT room temperature.16: m.p. 81 ± 83 8C (hexane). A referee proposed that we examine the reaction of S 8 O with trapping reagents, with regard to the mechanism of the reactions reported here. The reaction of S 8 O, prepared by a reported method, [4b] with 2,3dimethyl-1,3-butadiene in dichloromethane at room temperature for 1 h gave 2 in only 1.4 % yield, while that carried out under reflux gave 2 in 25 % yield. At present we do not have direct evidence for the existence of free S 2 O in solution, so that ªS 2 Oº should be read as ªS 2 O equivalentº throughout this paper.

show abstract

Section: Rhodium-catalyzed Hydrophosphorylation Ofmentioning

confidence: 99%

Solid-State Isomerization of Atropodiastereomers: Effective Diastereoselection through Polymorphic Transformations

et al. 2001

View full text Add to dashboard Cite

show abstract

“…Dodson has found that disulfur monoxide undergoes an inefficient 4 + 2 cycloaddition with dienes, e.g., as shown in Eq. 7-72 (Dodson et al, 1972). Reactions involving sulfur S 0 3 · dioxane (7-71) O SO,…”

Section: R E a C T I O N S Involving Other Sulfur O X I D E Smentioning

confidence: 99%

Pericyclic Reactions of Organosulfur Compounds

1978

Organic Chemistry: A Series of Monographs

View full text Add to dashboard Cite

“… Up to now, the use of S 2 O in organic chemistry has been limited to reactions with a few 1,3‐butadienes 2. One reason for this is probably the troublesome methods for its generation; for example, pyrolysis of ethylene episulfoxide,2 electronic discharge of SO 2 ,3 and reactions of heavy metal oxides or sulfides with elemental sulfur at 250–400 °C or with gaseous SOCl 2 at 160 °C and 0.5 Torr 3…”

mentioning

confidence: 99%

“…Then, 2,3‐dimethyl‐ or 2,3‐diphenyl‐1,3‐butadiene (11 and 3 molar equiv, respectively) was added, and the mixture was warmed to room temperature. Workup gave the adducts 2 and 6 2 in 33 and 27 % yield, respectively [Eq. (1)rsqb;.…”

mentioning

confidence: 99%

A Convenient Method for the Generation of a Disulfur Monoxide Equivalent and Its Reaction with Diazoalkanes to Yield Dithiirane 1-Oxides

Ishii

Kawai

Tekura

et al. 2001

Angew. Chem. Int. Ed.

View full text Add to dashboard Cite

show abstract

Disulfur monoxide. Reaction with dienes

Abstract: Disulfur monoxide (S20) reacts with 2,3-disubstituted butadienes to form 4,5-disubstituted 3,6-dihydro-l,2dithiin 1-oxides. The structure of 4,5-diphenyi-3,6-dihydro-1,2-dithiin 1-oxide (3) was established by independent synthesis. Reaction of cisor Show more

Cited by 45 publications

References 0 publications

Solid-State Isomerization of Atropodiastereomers: Effective Diastereoselection through Polymorphic Transformations

Solid-State Isomerization of Atropodiastereomers: Effective Diastereoselection through Polymorphic Transformations

Pericyclic Reactions of Organosulfur Compounds

A Convenient Method for the Generation of a Disulfur Monoxide Equivalent and Its Reaction with Diazoalkanes to Yield Dithiirane 1-Oxides

Contact Info

Product

Resources

About