Further Ab initio studies on the reactivity of nitrosoketene

Sihyun Ham; David M. Birney

doi:10.1016/S0040-4039(97)01444-5

Further Ab initio studies on the reactivity of nitrosoketene

Sihyun Ham, David M. Birney

Chemistry and Biochemistry

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

21 Scopus citations

Abstract

The cycloadditions of nitrosoketene with formaldehyde, acetone and 2-propenal were calculated using ab initio molecular orbital theory (MP2/6-31G*). The reactions proceed by the [3+2] pathway via a concerted, planar and pseudopericyclic transition state with a significantly lower barrier rather than by the alternative [4+2]. The transition state asynchronicity can be used to explain the substituent effects on the cycloaddition of ketones with nitrosoketene.

Original language	English
Pages (from-to)	5925-5928
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(97)01444-5
State	Published - Aug 1997

Access to Document

10.1016/S0040-4039(97)01444-5

Cite this

@article{fec0557739314d4e8fcd1dfff3ad622e,

title = "Further Ab initio studies on the reactivity of nitrosoketene",

abstract = "The cycloadditions of nitrosoketene with formaldehyde, acetone and 2-propenal were calculated using ab initio molecular orbital theory (MP2/6-31G*). The reactions proceed by the [3+2] pathway via a concerted, planar and pseudopericyclic transition state with a significantly lower barrier rather than by the alternative [4+2]. The transition state asynchronicity can be used to explain the substituent effects on the cycloaddition of ketones with nitrosoketene.",

author = "Sihyun Ham and Birney, {David M.}",

note = "Funding Information: Acknowledgment. This research was supported by a grant from the Robert A. Welch Foundation. We thank for Professor Katagiri for stimulating discussions.",

year = "1997",

month = aug,

doi = "10.1016/S0040-4039(97)01444-5",

language = "English",

volume = "38",

pages = "5925--5928",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "34",

}

TY - JOUR

T1 - Further Ab initio studies on the reactivity of nitrosoketene

AU - Ham, Sihyun

AU - Birney, David M.

N1 - Funding Information: Acknowledgment. This research was supported by a grant from the Robert A. Welch Foundation. We thank for Professor Katagiri for stimulating discussions.

PY - 1997/8

Y1 - 1997/8

N2 - The cycloadditions of nitrosoketene with formaldehyde, acetone and 2-propenal were calculated using ab initio molecular orbital theory (MP2/6-31G*). The reactions proceed by the [3+2] pathway via a concerted, planar and pseudopericyclic transition state with a significantly lower barrier rather than by the alternative [4+2]. The transition state asynchronicity can be used to explain the substituent effects on the cycloaddition of ketones with nitrosoketene.

AB - The cycloadditions of nitrosoketene with formaldehyde, acetone and 2-propenal were calculated using ab initio molecular orbital theory (MP2/6-31G*). The reactions proceed by the [3+2] pathway via a concerted, planar and pseudopericyclic transition state with a significantly lower barrier rather than by the alternative [4+2]. The transition state asynchronicity can be used to explain the substituent effects on the cycloaddition of ketones with nitrosoketene.

UR - http://www.scopus.com/inward/record.url?scp=0030741105&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)01444-5

DO - 10.1016/S0040-4039(97)01444-5

M3 - Article

AN - SCOPUS:0030741105

SN - 0040-4039

VL - 38

SP - 5925

EP - 5928

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Further Ab initio studies on the reactivity of nitrosoketene

Abstract

Access to Document

Other files and links

Fingerprint

Cite this