Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds

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Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds. / Jørgensen, Flemming S.; Gajhede, Michael; Frei, Bruno.

In: Helvetica Chimica Acta, Vol. 68, No. 8, 01.01.1985, p. 2148-2157.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Jørgensen, FS, Gajhede, M & Frei, B 1985, 'Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds', Helvetica Chimica Acta, vol. 68, no. 8, pp. 2148-2157. https://doi.org/10.1002/hlca.19850680809

APA

Jørgensen, F. S., Gajhede, M., & Frei, B. (1985). Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds. Helvetica Chimica Acta, 68(8), 2148-2157. https://doi.org/10.1002/hlca.19850680809

Vancouver

Jørgensen FS, Gajhede M, Frei B. Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds. Helvetica Chimica Acta. 1985 Jan 1;68(8):2148-2157. https://doi.org/10.1002/hlca.19850680809

Author

Jørgensen, Flemming S. ; Gajhede, Michael ; Frei, Bruno. / Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds. In: Helvetica Chimica Acta. 1985 ; Vol. 68, No. 8. pp. 2148-2157.

Bibtex

@article{e6ec646bb7e8473eb1ce6b6d6affb898,
title = "Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds",
abstract = "The He(I) PE spectra of 1,3‐dioxepine (1) and the related bicyclic acetals 1,3,7,7‐tetramethyl‐2,11‐dioxabicyclo[4.41]undeca‐3,5‐dien‐10‐one (2) and 1,3,7,7‐tetramethyl‐10‐methylidene‐2,11‐dioxabicyclo[4.4.1]undeca‐3,5‐diene (3) have been recorded and analyzed. Interpretation of the PE data indicate strong orbital interactions between the diene and acetal moieties in 1. Different conformations have been evaluated by a joint MMP2 molecular mechanics and ab initio molecular orbital analysis, which shows 1 to prefer a slightly boat‐shaped conformation with the diene part being planar and the CH2 group placed considerably out‐of‐plane. The bicyclic acetals 2 and 3 show a frontier orbital picture similar to 1 superimposed with the characteristics of the CO and CC groups, respectively. The crystal structure of the keto‐acetal 2 was determined by an X‐ray analysis.",
author = "J{\o}rgensen, {Flemming S.} and Michael Gajhede and Bruno Frei",
year = "1985",
month = "1",
day = "1",
doi = "10.1002/hlca.19850680809",
language = "English",
volume = "68",
pages = "2148--2157",
journal = "Helvetica Chimica Acta",
issn = "0018-019X",
publisher = "VerlagHelvetica Chimica Acta",
number = "8",

}

RIS

TY - JOUR

T1 - Cyclic Acetals. Structural Analysis of 1,3‐Dioxepine and Related Compounds

AU - Jørgensen, Flemming S.

AU - Gajhede, Michael

AU - Frei, Bruno

PY - 1985/1/1

Y1 - 1985/1/1

N2 - The He(I) PE spectra of 1,3‐dioxepine (1) and the related bicyclic acetals 1,3,7,7‐tetramethyl‐2,11‐dioxabicyclo[4.41]undeca‐3,5‐dien‐10‐one (2) and 1,3,7,7‐tetramethyl‐10‐methylidene‐2,11‐dioxabicyclo[4.4.1]undeca‐3,5‐diene (3) have been recorded and analyzed. Interpretation of the PE data indicate strong orbital interactions between the diene and acetal moieties in 1. Different conformations have been evaluated by a joint MMP2 molecular mechanics and ab initio molecular orbital analysis, which shows 1 to prefer a slightly boat‐shaped conformation with the diene part being planar and the CH2 group placed considerably out‐of‐plane. The bicyclic acetals 2 and 3 show a frontier orbital picture similar to 1 superimposed with the characteristics of the CO and CC groups, respectively. The crystal structure of the keto‐acetal 2 was determined by an X‐ray analysis.

AB - The He(I) PE spectra of 1,3‐dioxepine (1) and the related bicyclic acetals 1,3,7,7‐tetramethyl‐2,11‐dioxabicyclo[4.41]undeca‐3,5‐dien‐10‐one (2) and 1,3,7,7‐tetramethyl‐10‐methylidene‐2,11‐dioxabicyclo[4.4.1]undeca‐3,5‐diene (3) have been recorded and analyzed. Interpretation of the PE data indicate strong orbital interactions between the diene and acetal moieties in 1. Different conformations have been evaluated by a joint MMP2 molecular mechanics and ab initio molecular orbital analysis, which shows 1 to prefer a slightly boat‐shaped conformation with the diene part being planar and the CH2 group placed considerably out‐of‐plane. The bicyclic acetals 2 and 3 show a frontier orbital picture similar to 1 superimposed with the characteristics of the CO and CC groups, respectively. The crystal structure of the keto‐acetal 2 was determined by an X‐ray analysis.

UR - http://www.scopus.com/inward/record.url?scp=84987493226&partnerID=8YFLogxK

U2 - 10.1002/hlca.19850680809

DO - 10.1002/hlca.19850680809

M3 - Journal article

AN - SCOPUS:84987493226

VL - 68

SP - 2148

EP - 2157

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

SN - 0018-019X

IS - 8

ER -

ID: 218713809