6‐Fulvenselon

Schulz, Reinhard; Schweig, Armin

doi:10.1002/ange.19800920115

Cited by 17 publications

(3 citation statements)

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“…114.9, 121.5, 123.3, 125.4, 127.0, 153.9. Photoelectron spectroscopic data for ( 1 ) and (3): (7): 8.77 (n), 9.48 (n), 10.14, 10.97 eV; (3): 8.84 (n), 9.55 (n), 10.80 (no), 11.12 (n) eV. The pyrolysis of o-chloromethyltoluenes to give o-xylylenes and their thermal dimerization, either inter-or intramolecularly, has proved to be an extremely useful synthetic sequence for preparing [2,]cyclophanes[''.…”

Section: Methodsmentioning

confidence: 99%

“…Silica gel chromatography followed by fractional crystallization from ethyl acetate cleanly separates isomers (5) and (6). Conversion of (5) to the corresponding hydroxymethyl derivative (7) (m. p. =290-291 "C) was readily accomplished using lithium aluminum hydride in ether. Similarly, treatment of (7) with SOCI, easily gave the chloride (8) (m. p. = 252 "C, decomp.).…”

Section: 13-mentioning

confidence: 99%

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4,13‐Diaza[2₄](1,2,4,5)cyclophane and 4,16‐Diaza[2₄](1,2,4,5)‐cyclophane

Kang

Boekelheide

1981

Angew. Chem. Int. Ed. Engl.

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Section: Methodsmentioning

confidence: 99%

Section: 13-mentioning

confidence: 99%

4,13‐Diaza[2₄](1,2,4,5)cyclophane and 4,16‐Diaza[2₄](1,2,4,5)‐cyclophane

Kang

Boekelheide

1981

Angew. Chem. Int. Ed. Engl.

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“…114.9, 121.5, 123.3, 125.4, 127.0, 153.9. Photoelectron spectroscopic data for ( 1 ) and (3): (7): 8.77 (n), 9.48 (n), 10.14, 10.97 eV; (3): 8.84 (n), 9.55 (n), 10.80 (no), 11.12 (n) eV.…”

Section: Methodsmentioning

confidence: 99%

Cyclopentadienethione

Schulz¹,

Schweig²

1981

Angew. Chem. Int. Ed. Engl.

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We report here the first synthesis of cyclopentadienethione (2)[11. It is formed by gas phase pyrolysis (VTPES methodr2], reactor ca. 20x0.5 cm, 0.05 mbar pressure) of 1,2,3-benzoxadithiol 2-oxide (1) and 1,3-benzoxathiol-2-(3).(2) is unambiguously characterized from its photoelectron spectrum ( Fig. Ib and d). Band @ (at 8.87 ev), due to its shape, position and energy-dependence of the intensi-tyC4], is unequivocally the 'B2(ns)-band. Band @ (at 9.18 ev) is, because of its position (expected at 9.2 eV from the position of the corresponding band in cyclopentadien~ne[~~ and from the ca. 0.2 eV smaller inductive effect of the thiocarbonyl group[61), assigned as an 'A,(n)-band. Band @ (at 10.35 ev) is identified from a relati~nship"~ for the 'B,(n)ionization energy of fulvene-type molecules-again in excellent agreement with the measured value-expected at 10.4 eV, as a 'B,(n)-band. These conclusions are corroborated by CNDO/S-f8"1, MNDO-[8b1 and PERTCI[%alculations (Fig. 2).Thermal fragmentation of (1) and (3) probably proceeds['] via the monothiobenzoquinone (4)lo1. From MNDO-calculations, the valence isomeric benzoxathiete (S) is considerably more energy-rich than (4); the thiocar-bony1 compounds (2) and (4) have ca. 50 kcal/mol more energy than the carbonyl compounds cyclopentadienone and 1,2-benzoquinone. In fact, when (1) is pyrolyzed be-[' I Prof. Dr. A. Schweig, Dip1.-Chem. R. Schulz

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