Preparation and Some Subsequent Transformations of Tetraethynylmethane

Ken S. Feldman, Carolyn K. Weinreb, Wiley J. Youngs, John D. Bradshaw

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

Original languageEnglish (US)
Pages (from-to)9019-9026
Number of pages8
JournalJournal of the American Chemical Society
Volume116
Issue number20
DOIs
StatePublished - Oct 1 1994

Fingerprint

Acetylene
Ketones
Transition metals
Metals
Derivatives

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Feldman, K. S., Weinreb, C. K., Youngs, W. J., & Bradshaw, J. D. (1994). Preparation and Some Subsequent Transformations of Tetraethynylmethane. Journal of the American Chemical Society, 116(20), 9019-9026. https://doi.org/10.1021/ja00099a020
Feldman, Ken S. ; Weinreb, Carolyn K. ; Youngs, Wiley J. ; Bradshaw, John D. / Preparation and Some Subsequent Transformations of Tetraethynylmethane. In: Journal of the American Chemical Society. 1994 ; Vol. 116, No. 20. pp. 9019-9026.
@article{4c6a5d6e891242a2a250f77ac251de11,
title = "Preparation and Some Subsequent Transformations of Tetraethynylmethane",
abstract = "Tetraethynylmethane (1) was synthesized in 10 steps and 33{\%} overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.",
author = "Feldman, {Ken S.} and Weinreb, {Carolyn K.} and Youngs, {Wiley J.} and Bradshaw, {John D.}",
year = "1994",
month = "10",
day = "1",
doi = "10.1021/ja00099a020",
language = "English (US)",
volume = "116",
pages = "9019--9026",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "20",

}

Feldman, KS, Weinreb, CK, Youngs, WJ & Bradshaw, JD 1994, 'Preparation and Some Subsequent Transformations of Tetraethynylmethane', Journal of the American Chemical Society, vol. 116, no. 20, pp. 9019-9026. https://doi.org/10.1021/ja00099a020

Preparation and Some Subsequent Transformations of Tetraethynylmethane. / Feldman, Ken S.; Weinreb, Carolyn K.; Youngs, Wiley J.; Bradshaw, John D.

In: Journal of the American Chemical Society, Vol. 116, No. 20, 01.10.1994, p. 9019-9026.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Preparation and Some Subsequent Transformations of Tetraethynylmethane

AU - Feldman, Ken S.

AU - Weinreb, Carolyn K.

AU - Youngs, Wiley J.

AU - Bradshaw, John D.

PY - 1994/10/1

Y1 - 1994/10/1

N2 - Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

AB - Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

UR - http://www.scopus.com/inward/record.url?scp=0000408120&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000408120&partnerID=8YFLogxK

U2 - 10.1021/ja00099a020

DO - 10.1021/ja00099a020

M3 - Article

AN - SCOPUS:0000408120

VL - 116

SP - 9019

EP - 9026

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 20

ER -