Organometallic compounds of Group III. XIX. Regiospecificity and stereochemistry in the hydralumination of unsymmetrical acetylenes. Controlled cis or trans reduction of 1-alkynyl derivatives

Eisch, John J.; Foxton, M. W.

doi:10.1021/jo00822a012

Cited by 153 publications

(40 citation statements)

References 3 publications

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“…[18,19] In most cases the cis products are found, but in certain cases the trans isomer is observed. [20,21] Depending on the Scheme 1 amount of reducing agent, we were able to steer the reaction to yield either the monoenes or the dienes (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Preparation and Structures of Cyclic Tetrathiadienes and Tetrathiaenynes

2002

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Section: Resultsmentioning

confidence: 99%

Preparation and Structures of Cyclic Tetrathiadienes and Tetrathiaenynes

2002

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“…Namely, diiodobenzene (9) was coupled with one equivalent of trimethylsilylacetylene giving rise to o-iodo(trimethylsilylethynyl)benzene (11). The ethynylbenzene (11) was hydraluminated with DIBAL-H in hexane, [29][30][31] and then brominated with NBS 8,9,32,33) to afford tively. The remaining iodine moiety on 12 was converted to a bromotrimethylsilylethenyl group by the same procedure via 13 to afford 14 in 39% yields from 12.…”

Section: )mentioning

confidence: 99%

A Versatile Route to 3-Benzoheteroepines Containing Group 15 and 16 Heavier Elements Involving Several Novel Ring Systems, and Their Thermal Stabilities

Yasuike

Kiharada

Tsuchiya

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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The C-unsubstituted 3-benzoheteroepines (2a-g) containing group 15 (P, As, Sb, and Bi) and group 16 (S, Se, and Te) heavier elements were prepared by the reaction of the corresponding metal reagents with (Z,Z)-obis(b b-lithiovinyl)benzene (5) which was derived in two steps from a common o-phthalaldehyde (3). The heteroepines (2) thus obtained were thermally labile towards heteroatom extrusion, and their half-lives on heating estimated from 1 H-NMR spectral analysis showed that the 3-benzoheteroepines (2) were far less stable than the corresponding 1-benzoheteroepines (1). The 2,4-bis(trimethylsilyl)-3-benzoheteroepines (17) containing Sb, Bi, and Te were also prepared from o-diiodobenzene (9) in 6 steps and were found to be more stable than the corresponding C-unsubstituted heteroepines (2).

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“…In some cases the exclusive formation of one of the possible isomers was observed. The following heterocyclic systems were formed: 3-benzotellurepine (1) 14a , 1-benzotellurepine (2) 14b-d , tellurochromenes (3) 14b , benzotellurophenes (4 14e , 5 14f ), tellurophthalides (6) 14g , tellurochromones (7) 14h , iso-tellurochromenes (8) 14i,g , telluroindanes (9) 14i,j and benzotellurazepines (10) 14l (Scheme 12). .…”

Section: Intramolecular Hydrotellurationmentioning

confidence: 99%

Hydrotelluration of alkynes: a unique route to Z-vinyl organometallics

Vieira¹,

Zinn²,

Comasseto³

2001

J. Braz. Chem. Soc.

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A reação de hidroteluração de alquinos é revisada. A transformação de teluretos vinílicos em organometálicos vinílicos reativos e as reações de acoplamento de teluretos vinílicos com alquinos e organometálicos são apresentadas.The hydrotelluration reaction of alkynes is reviewed. The transformation of vinylic tellurides into reactive vinyl organometallics and the coupling reactions of vinylic tellurides with alkynes and organometallics are presented.

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Organometallic compounds of Group III. XIX. Regiospecificity and stereochemistry in the hydralumination of unsymmetrical acetylenes. Controlled cis or trans reduction of 1-alkynyl derivatives

Cited by 153 publications

References 3 publications

Preparation and Structures of Cyclic Tetrathiadienes and Tetrathiaenynes

Preparation and Structures of Cyclic Tetrathiadienes and Tetrathiaenynes

A Versatile Route to 3-Benzoheteroepines Containing Group 15 and 16 Heavier Elements Involving Several Novel Ring Systems, and Their Thermal Stabilities

Hydrotelluration of alkynes: a unique route to Z-vinyl organometallics

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