Thioaldehyde Diels-Alder Reactions

E. Vedejs; T. H. Eberlein; D. J. Mazur; C. K. McClure; D. A. Perry; R. Ruggeri; E. Schwartz; J. S. Stults; D. L. Varie; R. G. Wilde; S. Wittenberger

doi:10.1021/jo00359a034

Thioaldehyde Diels-Alder Reactions

E. Vedejs, T. H. Eberlein, D. J. Mazur, C. K. McClure, D. A. Perry, R. Ruggeri, E. Schwartz, J. S. Stults, D. L. Varie, R. G. Wilde, S. Wittenberger

School of Science, Engineering & Technology (Harrisburg)

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

135 Scopus citations

Abstract

Thioaldehydes containing virtually any a-substitutent can be generated by photofragmentation of phenacyl sulfides. Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advanced C-C bonding in the transition state. Acceptor-substituted thioaldehydes react in the opposite regiochemical sense with C-S bonding advanced. A number of unusual thioaldehydes have been trapped, including the parent HCH=S, Me₃SiCHS, Ph₂P(O)CH=S, PhSO₂CH=S, and CNCH=S, as well as more conventional alkyl- or acyl-substituted derivatives.

Original language	English (US)
Pages (from-to)	1556-1562
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	51
Issue number	9
DOIs	https://doi.org/10.1021/jo00359a034
State	Published - 1986

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00359a034

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title = "Thioaldehyde Diels-Alder Reactions",

abstract = "Thioaldehydes containing virtually any a-substitutent can be generated by photofragmentation of phenacyl sulfides. Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advanced C-C bonding in the transition state. Acceptor-substituted thioaldehydes react in the opposite regiochemical sense with C-S bonding advanced. A number of unusual thioaldehydes have been trapped, including the parent HCH=S, Me3SiCHS, Ph2P(O)CH=S, PhSO2CH=S, and CNCH=S, as well as more conventional alkyl- or acyl-substituted derivatives.",

author = "E. Vedejs and Eberlein, {T. H.} and Mazur, {D. J.} and McClure, {C. K.} and Perry, {D. A.} and R. Ruggeri and E. Schwartz and Stults, {J. S.} and Varie, {D. L.} and Wilde, {R. G.} and S. Wittenberger",

year = "1986",

doi = "10.1021/jo00359a034",

language = "English (US)",

volume = "51",

pages = "1556--1562",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Thioaldehyde Diels-Alder Reactions

AU - Vedejs, E.

AU - Eberlein, T. H.

AU - Mazur, D. J.

AU - McClure, C. K.

AU - Perry, D. A.

AU - Ruggeri, R.

AU - Schwartz, E.

AU - Stults, J. S.

AU - Varie, D. L.

AU - Wilde, R. G.

AU - Wittenberger, S.

PY - 1986

Y1 - 1986

N2 - Thioaldehydes containing virtually any a-substitutent can be generated by photofragmentation of phenacyl sulfides. Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advanced C-C bonding in the transition state. Acceptor-substituted thioaldehydes react in the opposite regiochemical sense with C-S bonding advanced. A number of unusual thioaldehydes have been trapped, including the parent HCH=S, Me3SiCHS, Ph2P(O)CH=S, PhSO2CH=S, and CNCH=S, as well as more conventional alkyl- or acyl-substituted derivatives.

AB - Thioaldehydes containing virtually any a-substitutent can be generated by photofragmentation of phenacyl sulfides. Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advanced C-C bonding in the transition state. Acceptor-substituted thioaldehydes react in the opposite regiochemical sense with C-S bonding advanced. A number of unusual thioaldehydes have been trapped, including the parent HCH=S, Me3SiCHS, Ph2P(O)CH=S, PhSO2CH=S, and CNCH=S, as well as more conventional alkyl- or acyl-substituted derivatives.

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U2 - 10.1021/jo00359a034

DO - 10.1021/jo00359a034

M3 - Article

AN - SCOPUS:33845374421

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VL - 51

SP - 1556

EP - 1562

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Thioaldehyde Diels-Alder Reactions

Abstract

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