Chemistry of .alpha.,.beta.-unsaturated thione dimers. 1. Preparation of .alpha.,.beta.-unsaturated thione dimers and thermolysis of these dimers in the presence of acrylonitrile or acrylamide

Karakasa, Takayuki; Motoki, Shinichi

doi:10.1021/jo00415a036

Cited by 64 publications

(10 citation statements)

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“…7-166.5 °C;IR (KBr): 2918, 2863, 2832, 530 cm -1 ; 1 H NMR (400 MHz, CDCl3) δ 3.09 (d,2 JHP = 11.0 Hz,2H), 3.88 (s, 3H), 7.06 (d,J = 8.8 Hz,2H),7.55 (d,J = 8.8 Hz,2H); 13 C NMR (100 MHz, CDCl3) δ 42.7 (d,1 JCP = 53.4 Hz), 55.9, 69.9 (ddd, 2 JCP = 8.2 Hz, 2 JCP = 8.2 Hz, 2 JCP = 8.2 Hz), 115.9 (×2), 127.2 (×2), 132.3 (ddd, 3 JCP = 21.1 Hz, 3 JCP = 8.1 Hz, 3 JCP = 8.1 Hz), 162.1; 31 P NMR (160 MHz, CDCl3) δ 57.5, 62.6; HRMS-ESI (m/z): [M + H] + calcd for C9H10OP3S8: 482.7710, found: 482.7723; Anal Cacld for C9H9OP3S8: C, 22.40;H,1.88. Found: C,22.15;H,4,6,8,3,5triphosphaadamantane 1,3,.…”

Section: General Procedures 2: Synthesis Of 2 (Short Silica Gel Columnmentioning

confidence: 99%

“…4-171.7 °C;IR (KBr): 2916, 2864, 527 cm -1 ; 1 H NMR (400 MHz, CDCl3) δ 2.44 (s, 3H), 3.11 (d,2 JHP = 11.0 Hz,2H) 23.17;H,1.94. Found: C,22.97;H,4,6,8,3,5triphosphaadamantane 1,3,. dihydro-2,6epithio [1,2,5]thiadiphospholo [2,3-d] [1,3,2,4]dithiadiphosphole 2, 4,6-trisulfide (5).…”

Section: General Procedures 2: Synthesis Of 2 (Short Silica Gel Columnmentioning

confidence: 99%

“…Using Procedure 1; Yield: 5% (76.2 mg), Colorless crystal; MP 213.9-214.4 °C; IR (KBr): 2929, 2912, 2826, 1459, 750, 692, 528 cm -1 ; 1 H NMR (400 MHz, CDCl3) δ 3.38 (ddd, 2 JHP = 39.6 Hz, 14.4 Hz, 3 JHP = 10.4 Hz, 1H), 3.87 (s, 3H), 4.46 (dd, J = 14. 4 Hz, 2 JHP = 12.0 Hz, 1H), 7.03 (d, J = 8.0 Hz, 1H), 7.09 (dd, J = 7.4, 7.4 Hz, 1H), 7.35-7.40 (m, 1H), 7.49-7.54 (m, 1H); 13 C NMR (100 MHz, CDCl3) δ 55.2 (dd, 1 JCP = 50.3 Hz, 2 JCP = 11.4 Hz), 55.6, 113.0 (d, J = 2.9 Hz), 119.9-120.0 (m), 121.8 (d, J = 2.0 Hz), 126.9 (d, J = 6.7 Hz), 132.7 (d,J = 3.8 Hz), 156.7 (d,J = 4.7 Hz), The quaternary carbon peak was not observed; 31…”

Section: General Procedures 2: Synthesis Of 2 (Short Silica Gel Columnmentioning

confidence: 99%

“…2 In another instance, Motoki and coworkers reported that the thionation of chalcone with tetraphosphorus decasulfide (P4S10, Berzelius reagent) 3 in carbon disulfide proceeded readily to give the corresponding thione dimer in moderate yield. 4 On the other hand, experimental and theoretical observations have indicated that neighboring group effects influenced the stability and the reactivity of the thiocarbonyl group. [5][6][7] Moreover, the electronic effects of the neighboring functional groups, 8 such as the 4,4'bis(N,N-dimethylamino)phenyl group of thio-Michler's ketone, 8c have also been involved in the stability of the thiocarbonyl group.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon

et al. 2017

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The synthesis of novel adamantane-like cage compounds consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2'-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4'dimethoxybenzophenone and N,N-dimethylbenzamide were successfully transformed into the corresponding thioketone (98%) and benzothioamide (89%), respectively.

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Section: General Procedures 2: Synthesis Of 2 (Short Silica Gel Columnmentioning

confidence: 99%

Section: General Procedures 2: Synthesis Of 2 (Short Silica Gel Columnmentioning

confidence: 99%

Section: General Procedures 2: Synthesis Of 2 (Short Silica Gel Columnmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon

et al. 2017

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“…Also, the thermolysis of thiochalcone dimers and 2-arylbenzylidene-1-thiotetralone dimers in the presence of acrylonitrile or acrylamide was reported. 10 On the other hand, the reaction of some chalcones, 2-arylbenzylidene-1-tetralones and 2,2-dialkyl-3-arylbenzylidene-4-chromanones with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide (Lawesson's reagent, LR) was reported. 11,12 Recently, some new chromenothiapyran derivatives have been reported.…”

Section: Introductionmentioning

confidence: 99%

[4 + 2] Cycloaddition Reactions Involving 2-Arylmethylidene-1-thiooxoindan Intermediates and Antimicrobial Activity Evaluation of Some Products

Hegab

Elmalah

Gad

2009

Phosphorus, Sulfur, and Silicon and the Related Elements

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dimers 5a-c were prepared by the reaction of the corresponding α,β-unsaturated ketones 3a-c with Lawesson' Reagent (LR) in refluxing benzene. When these dimers were refluxed with LR in xylene, the 1,2-thiaphospholene-2-sulfides 7a-c were obtained. On the other hand, the thermolysis of the dimers 5a-c in the presence of acrylamide or dichloromaleic anhydride gave the corresponding cycloadducts of Diels-Alder type 8a-c, and 10a-c, respectively. The 3-carbamoyl thiapyran derivatives 8a-c showed good antimicrobial activity.

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The Retro–Diels–Alder Reaction PartI.CCDienophiles

Rickborn

1998

Organic Reactions

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The Diels–Alder (“DA”) reaction is so familiar to organic chemists that the retro‐Diels–Alder or retro‐diene reaction (hereafter “rDA”) requires no conceptual introduction. However, a working definition is needed to indicate the coverage of this review. The intent is to include all reported examples of the general skeletal process excluded in this chapter. Any of the atoms in the starting material (cycloadduct) may be carbon or heteroatom, and substituents on all positions are allowed. In addition, any bond order available to the element in any oxidation state is included, as well as bonding to non‐nearest neighbor atoms (bicyclics, etc.). The volume of literature required separation of this review into two parts. Part I covers all expelled C–C dienophiles, i.e. those reactions that generate a new carbon‐carbon double or triple bond in the dienophile that is formed. Part II, to appear later, covers those expelled dienophiles in which one or both atoms is a heteroatom. Certain specific topics are intentionally omitted. These are: rDA reactions invoked under mass spectral conditions; rDA reactions of polymeric substrates; Electrocyclic processes, some of which are arguably very similar to rDA reactions (these are not addressed unless needed for clarification of an rDA sequence); and a thorough discussion of homo‐rDA reactions. CAS‐Online searches resulted in ca. 1,300 references, of which ca. 900 proved pertinent to the rDA topic as defined and delimited above. Active literature searching was halted in April 1995, but occasional more recent articles are included. Over 2,500 pertinent references were eventually found. Most were obtained by perusal of primary literature (articles) and secondary sources (books and reviews). Computer based search success was limited mainly by the failure of authors or abstractors to key‐word this topic, an especially common occurrence when the expelled dienophile was a simple substance such as N 2 or CO 2 . Overall, approximately 3,500 books, chapters, reviews, articles, and abstracts were consulted in an effort to make this review as comprehensive as possible. This was done with the certainty that some pertinent literature would be missed, tempered by the view that these omissions are probably also lost to any future rational search method. Many secondary sources proved valuable not only for in‐depth discussion of certain rDA reaction types, but also for providing comparisons with related topics. To assist the reader, these secondary sources are referenced (alphabetically by first author within broad subject areas) with a title or brief note on the topic(s) addressed. The first group lists earlier reviews with primary focus on rDA reactions, followed by items of Historical/General Interest, reviews that deal with Experimental Methods, DA reactions (general and specific), reviews of Related Topics (these impinge in more or less significant ways on rDA reactions), and general treatments of Theory and Mechanism.

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Chemistry of .alpha.,.beta.-unsaturated thione dimers. 1. Preparation of .alpha.,.beta.-unsaturated thione dimers and thermolysis of these dimers in the presence of acrylonitrile or acrylamide

Cited by 64 publications

References 2 publications

Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon

Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon

[4 + 2] Cycloaddition Reactions Involving 2-Arylmethylidene-1-thiooxoindan Intermediates and Antimicrobial Activity Evaluation of Some Products

The Retro–Diels–Alder Reaction PartI.CCDienophiles

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