3-exo,3′-exo-(1R,1′R)-Bithiocamphor — a versatile source for functionally different 3,3′-bibornane derivatives — I. Ring-closure reactions and prototropic rearrangements

Schroth, Werner; Hintzsche, E.; Spitzner, R.; Ströhl, Dieter; Sieler, Joachim

doi:10.1016/0040-4020(95)00852-y

Cited by 27 publications

(20 citation statements)

References 32 publications

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“…While cZt - 3b was twisted ca. 40° out of plane, tZt - 3b (not shown) was found to be planar; no energy minimum was found corresponding to cZc - 3b in either planar or twisted geometries. 6a,15a The frequencies and intensities calculated for the cZt - 3b geometry fit the experiments nicely 15a. An energy minimum was found for 9 in a slightly twisted s-cis geometry.…”

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confidence: 76%

“…The quantum yield for conversion of 3,6-diphenyl-1,2-dithiin ( 1c ) to 2,5-diphenylthiophene ( 2c ) is 0.91 4d ring opening of 1 to ( Z )-butenedithione derivatives ( 3 ) has been postulated, 2ab,6a and involvement of various valence isomers of 3 in the desulfurization process has been suggested. 6b-d As well, direct extrusion of singlet sulfur from 1b is calculated to be disfavored by ca. 80 kcal mol -1 6a. Exposure of 1a to visible light, leading to desulfurization, results in enhanced biological activity …”

mentioning

confidence: 99%

“…Electrocyclic ring opening followed by limited rotation about the C1−C2 bond could lead directly to cZt - 3b . Rotation in the opposite direction would afford cZc - 3b , disfavored relative to cZt - 3b . 2b,6a Compound cZt - 3b can then undergo either a 1,5-sigmatropic shift 13a, giving 9 or a π 4 a + π 2 a rearrangement giving 4b . Formation of 9 is apparently favored at 25 K in the Ar matrix.…”

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confidence: 99%

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Photochemistry of Thiarubrine A and Other 1,2-Dithiins: Formation of 2,6-Dithiabicyclo[3.1.0]hex-3-enes

et al. 1996

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confidence: 76%

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confidence: 99%

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Photochemistry of Thiarubrine A and Other 1,2-Dithiins: Formation of 2,6-Dithiabicyclo[3.1.0]hex-3-enes

et al. 1996

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“…The bond length changes in BzImS are of about this order of magnitudes, and these changes are compatible with the work energy of about 12 kJ mol –1 performed by the pressure of 2.0 GPa on the BzImS crystal. Our inspection of the CS bond in structures deposited in the Cambridge Crystallographic Database (CSD) shows clearly that they can be divided into compounds where the thione group is located in moieties of saturated C–C bonds, for example C sp 3 –C(S)–C sp 3 , − and a group where the thione bond is conjugated. − The effect of the zwitterionic contribution for the CS bond length is clearly observed in the crystal structure of 1,3-dibenzyl-2-(4′,4′-dimethyl-2′,6′-dithioxocyclohexylidene) hexahydropyrimidine (refcode LEVRIN), where CS distances become 1.667 and 1.641 Å . On the other hand, according to a survey of the CSD, the average length of double bond CS is 1.681 Å, nearly exactly as this in BzImS at 0.1 MPa and considerably longer than that in CS 2 – 1.546(1) Å at 5.3 K/0.1 MPa and 1.550(2) Å at 295 K /3.7 GPa .…”

Section: Resultsmentioning

confidence: 98%

High Pressure Effects on Zwitterionic and Thione Mesomeric Contributions in 2-Benzimidazole-2-Thione

Tomkowiak

Katrusiak

2017

J. Phys. Chem. C

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High pressure reduces the zwitterionic mesomeric contribution and increases the thione contribution in 2-benzimidazole-2-thione. These mesomeric changes are manifested in the shortened bond S–C and elongated bond C–N in the S–C–N moiety. These transformations are consistent with the le Chatelier law, as they counteract the increase of electrostatic interactions when the intermolecular distances between electronegative sulfur atoms and arene π-electrons are compressed. The changing interactions affect the crystal strain and its structural transformations. Consequently, the crystal compression and thermal expansion initially, until about 1.0 GPa, are inconsistent with the inverse relationship rule of pressure and temperature effects. Some anomalous features of the thermal expansion can be associated with isostructural transformations of the crystal.

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“…514 Some ring-closure and prototropic rearrangement reactions of 374 have been studied. 515 Irradiation of 374 at 254 nm has been found to give 378. 516 The ligands 379 have been synthesised and catalyse the enantioselective addition of diethylzinc to benzaldehyde to give (S)-1-phenylpropanol of 85-88% ee.…”

Section: Camphanes and Isocamphanesmentioning

confidence: 99%

Monoterpenoids

Grayson¹

1998

Nat. Prod. Rep.

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Species Principal constituents ReferenceAbies balsamea Mill -and -pinene, -phellandrene, limonene Achillea biebersteinii Afan piperitone, or cineol and camphor Aloysia triphylla (L'Herit.) Britton citral, limonene Alpinia conchigera Griff. cineol Alseuosmia macrophylla A. Cunn. flowers: linalool Ambrosia microcephala DC. camphor, bornyl acetate Amomum subulatum Roxb. cineol, -terpineol, -and -pinene Artemisia afra yomogi alcohol, artemisyl acetate Artemisia afra Willd. cineol, terpinen-4-ol, borneol Artemisia ordosica -and -pinene, sabinene Austromyrtus dulcis (C. T. White) L. S. Smith (chemotype) -pinene, cineol Boronia megastigma Nees. -ionone, 8-hydroxylinalyl esters, geranyloxy cinnamate Bouea macrophylla Griff. ( E)--ocimene, -pinene Calamintha cretica piperitenone, piperitenone oxide Calamintha incana (Sm.) Boiss. piperitenone oxide Callistemon speciosus Anthor. cineol, -pinene, -terpineol Canella winteriana Gaertn. stem and bark: cineol, terpinen-4-ol, -terpinyl acetate, -terpineol; leaves: myrcene Cedronella canariensis Webb et Berth. ssp. canariensis pinocarvone Chamelaucium uncinatum genotypes -pinene, citronellal, limonene, linalool, -terpinyl acetate Chenopodium ambrosioides limonene, trans-pinocarveol Chenopodium botrys -8 Chrysanthemum balsamata carvone, camphor Chrysanthemum lavandulaefolium menthol Cinnamomum camphora Nees et Ebermaier camphor, cineol, terpinen-4-ol, limonene Cinnamomum puciflorum -2 Citrus grandis limonene Clausena anisata (Willd.) J. D. Hook limonene, myrcene Coleus aromaticus carvacrol, camphor Coreopsis barteri Oliv. & Hiern limonene, -phellandrene Coreopsis grandis Hogg ex Sweet myrcene Coriandrum sativum seeds: linalool Coridothymus capitatus Reich. f. carvacrol 98, 99 Cunila fasiculata menthofuran Cunila microcephala menthofuran, limonene Curcuma aeruginosa Roxb. cineol, camphor Curcuma amada Roxb. myrcene Curcuma aromatica Salisb. cineol, camphor, isoborneol, camphene Curcuma cochinchinensis Gagnep. cineol Curcuma domestica -phellandrene, cineol, p-cymene, -pinene Curcuma pierreana Gagnep. Rhizome, stem: isoborneol, isobornyl acetate leaf: isoborneol, camphor Croton aubrevillei J. Leonard linalool Croton zambesicus Muell. Arg. linalool Cyclotrichum origanifolium (Labill.) Manden. et Scheng. cis-isopulegone, pulegone, isomenthone, menthol Cymbopogon caesius (Nees et Hook. et Arn.) Stapf. perillyl alcohol, geraniol, limonene Cymbopogon citratus (DC.) Stapf. citral, geraniol, myrcene, -and -pinene Cymbopogon khasianus (Munro ex Hack.) Bor. geraniol, geranyl acetate, linalool Cymbopogon schoenanthus piperitone, limonene Daphne mezereum flowers: linalool, linalyl oxides Echinophora chryantha Freyn et Sint. -phellandrene Egletes viscosa various terpenol acetates Elsholtzia ciliata (Thunb.) Hyland chemotype (a): elsholtzia ketone, -thujone chemotype (b): neral, geranial, limonene

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3-exo,3′-exo-(1R,1′R)-Bithiocamphor — a versatile source for functionally different 3,3′-bibornane derivatives — I. Ring-closure reactions and prototropic rearrangements

Cited by 27 publications

References 32 publications

Photochemistry of Thiarubrine A and Other 1,2-Dithiins: Formation of 2,6-Dithiabicyclo[3.1.0]hex-3-enes

Photochemistry of Thiarubrine A and Other 1,2-Dithiins: Formation of 2,6-Dithiabicyclo[3.1.0]hex-3-enes

High Pressure Effects on Zwitterionic and Thione Mesomeric Contributions in 2-Benzimidazole-2-Thione

Monoterpenoids

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