The absolute configuration of sulfoxides and sulfinates

Michael Axelrod, Paul Bickart, John Jacobus, Mark M. Green, Kurt Mislow

Research output: Contribution to journalArticle

Abstract

The absolute configurations of (-)-menthyl (-)-(S)-p-iodobenzenesulfinate and (-)-(R)-3-methylsulfinylpropylamine have been linked by a synthetic sequence involving an odd number of Grignard displacement reactions; consequently, this displacement has been rigorously shown to proceed with inversion of configuration at sulfur. This sequence, joined to present and earlier intercorrelations of sulfinates and sulfoxides, serves to establish absolute configurations in this series of compounds. The absolute configuration of (+)-methyl allyl sulfoxide, a key relay compound in the sequence, has been reassigned. Some apparent discrepancies which appeared in the earlier literature and which bear on the present work have been resolved.

Original languageEnglish (US)
Pages (from-to)4835-4842
Number of pages8
JournalJournal of the American Chemical Society
Volume90
Issue number18
StatePublished - 1968

Fingerprint

sulfoxide
Sulfoxides
Sulfur

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Axelrod, M., Bickart, P., Jacobus, J., Green, M. M., & Mislow, K. (1968). The absolute configuration of sulfoxides and sulfinates. Journal of the American Chemical Society, 90(18), 4835-4842.

The absolute configuration of sulfoxides and sulfinates. / Axelrod, Michael; Bickart, Paul; Jacobus, John; Green, Mark M.; Mislow, Kurt.

In: Journal of the American Chemical Society, Vol. 90, No. 18, 1968, p. 4835-4842.

Research output: Contribution to journalArticle

Axelrod, M, Bickart, P, Jacobus, J, Green, MM & Mislow, K 1968, 'The absolute configuration of sulfoxides and sulfinates', Journal of the American Chemical Society, vol. 90, no. 18, pp. 4835-4842.
Axelrod M, Bickart P, Jacobus J, Green MM, Mislow K. The absolute configuration of sulfoxides and sulfinates. Journal of the American Chemical Society. 1968;90(18):4835-4842.
Axelrod, Michael ; Bickart, Paul ; Jacobus, John ; Green, Mark M. ; Mislow, Kurt. / The absolute configuration of sulfoxides and sulfinates. In: Journal of the American Chemical Society. 1968 ; Vol. 90, No. 18. pp. 4835-4842.
@article{5b747d18a4fd4333b43c3928b93732fa,
title = "The absolute configuration of sulfoxides and sulfinates",
abstract = "The absolute configurations of (-)-menthyl (-)-(S)-p-iodobenzenesulfinate and (-)-(R)-3-methylsulfinylpropylamine have been linked by a synthetic sequence involving an odd number of Grignard displacement reactions; consequently, this displacement has been rigorously shown to proceed with inversion of configuration at sulfur. This sequence, joined to present and earlier intercorrelations of sulfinates and sulfoxides, serves to establish absolute configurations in this series of compounds. The absolute configuration of (+)-methyl allyl sulfoxide, a key relay compound in the sequence, has been reassigned. Some apparent discrepancies which appeared in the earlier literature and which bear on the present work have been resolved.",
author = "Michael Axelrod and Paul Bickart and John Jacobus and Green, {Mark M.} and Kurt Mislow",
year = "1968",
language = "English (US)",
volume = "90",
pages = "4835--4842",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - The absolute configuration of sulfoxides and sulfinates

AU - Axelrod, Michael

AU - Bickart, Paul

AU - Jacobus, John

AU - Green, Mark M.

AU - Mislow, Kurt

PY - 1968

Y1 - 1968

N2 - The absolute configurations of (-)-menthyl (-)-(S)-p-iodobenzenesulfinate and (-)-(R)-3-methylsulfinylpropylamine have been linked by a synthetic sequence involving an odd number of Grignard displacement reactions; consequently, this displacement has been rigorously shown to proceed with inversion of configuration at sulfur. This sequence, joined to present and earlier intercorrelations of sulfinates and sulfoxides, serves to establish absolute configurations in this series of compounds. The absolute configuration of (+)-methyl allyl sulfoxide, a key relay compound in the sequence, has been reassigned. Some apparent discrepancies which appeared in the earlier literature and which bear on the present work have been resolved.

AB - The absolute configurations of (-)-menthyl (-)-(S)-p-iodobenzenesulfinate and (-)-(R)-3-methylsulfinylpropylamine have been linked by a synthetic sequence involving an odd number of Grignard displacement reactions; consequently, this displacement has been rigorously shown to proceed with inversion of configuration at sulfur. This sequence, joined to present and earlier intercorrelations of sulfinates and sulfoxides, serves to establish absolute configurations in this series of compounds. The absolute configuration of (+)-methyl allyl sulfoxide, a key relay compound in the sequence, has been reassigned. Some apparent discrepancies which appeared in the earlier literature and which bear on the present work have been resolved.

UR - http://www.scopus.com/inward/record.url?scp=33947317936&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947317936&partnerID=8YFLogxK

M3 - Article

VL - 90

SP - 4835

EP - 4842

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 18

ER -