Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols

Sean P. Bew; G. Richard Stephenson; Jacques Rouden; Luis A. Martinez-Lozano; Haseena Seylani

doi:10.1021/ol400804b

Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols

Sean P. Bew, G. Richard Stephenson, Jacques Rouden, Luis A. Martinez-Lozano, Haseena Seylani

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

A much improved synthetic route to malonic acid half thioesters (MAHTs) and oxyesters (MAHOs), the easy incorporation of deuterium labeling expecially in MAHTs, and an unexpectedly large difference in enolization chemistry between MAHTs and MAHOs are reported. Density functional theory calculations explore the origins of this difference and identify an additional MAHT molecular orbital which increases delocalization between sulfur and the enol in both cisoid and transoid forms.

Original language	English
Pages (from-to)	3805-3807
Number of pages	3
Journal	Organic Letters
Volume	15
Issue number	15
DOIs	https://doi.org/10.1021/ol400804b
Publication status	Published - 2 Aug 2013

Access to Document

10.1021/ol400804b

Cite this

@article{e42bbffd18694ac0a2d6cb46f9835a20,

title = "Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols",

abstract = "A much improved synthetic route to malonic acid half thioesters (MAHTs) and oxyesters (MAHOs), the easy incorporation of deuterium labeling expecially in MAHTs, and an unexpectedly large difference in enolization chemistry between MAHTs and MAHOs are reported. Density functional theory calculations explore the origins of this difference and identify an additional MAHT molecular orbital which increases delocalization between sulfur and the enol in both cisoid and transoid forms.",

author = "Bew, {Sean P.} and Stephenson, {G. Richard} and Jacques Rouden and Martinez-Lozano, {Luis A.} and Haseena Seylani",

year = "2013",

month = aug,

day = "2",

doi = "10.1021/ol400804b",

language = "English",

volume = "15",

pages = "3805--3807",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols

AU - Bew, Sean P.

AU - Stephenson, G. Richard

AU - Rouden, Jacques

AU - Martinez-Lozano, Luis A.

AU - Seylani, Haseena

PY - 2013/8/2

Y1 - 2013/8/2

N2 - A much improved synthetic route to malonic acid half thioesters (MAHTs) and oxyesters (MAHOs), the easy incorporation of deuterium labeling expecially in MAHTs, and an unexpectedly large difference in enolization chemistry between MAHTs and MAHOs are reported. Density functional theory calculations explore the origins of this difference and identify an additional MAHT molecular orbital which increases delocalization between sulfur and the enol in both cisoid and transoid forms.

AB - A much improved synthetic route to malonic acid half thioesters (MAHTs) and oxyesters (MAHOs), the easy incorporation of deuterium labeling expecially in MAHTs, and an unexpectedly large difference in enolization chemistry between MAHTs and MAHOs are reported. Density functional theory calculations explore the origins of this difference and identify an additional MAHT molecular orbital which increases delocalization between sulfur and the enol in both cisoid and transoid forms.

UR - http://www.scopus.com/inward/record.url?scp=84881247972&partnerID=8YFLogxK

U2 - 10.1021/ol400804b

DO - 10.1021/ol400804b

M3 - Article

AN - SCOPUS:84881247972

SN - 1523-7060

VL - 15

SP - 3805

EP - 3807

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols

Abstract

Access to Document

Other files and links

Cite this