Grob-Type Fragmentation of Five- and Six-Membered Rings Promoted by Cuprous Ion

M. F. Semmelhack; J. C. Tomesch

doi:10.1021/jo00435a039

Grob-Type Fragmentation of Five- and Six-Membered Rings Promoted by Cuprous Ion

M. F. Semmelhack
, J. C. Tomesch

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

11 Scopus citations

Abstract

Copper(I) salts, especially the triflate and trifluoroacetate, promote efficient cleavage of 1-hydroxy-2-[bis- (phenylthio)methyl]cyclohexane and cyclopentane; a cyclic intermediate is unlikely, as complete reaction requires more than 2 mol equiv of copper(I); the product contains aldehyde and latent aldehyde units.

Original language	English (US)
Pages (from-to)	2657-2658
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	42
Issue number	15
DOIs	https://doi.org/10.1021/jo00435a039
State	Published - Jul 1 1977
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00435a039

Cite this

@article{8801ef2ff28b4007807653a0d0b38ca2,

title = "Grob-Type Fragmentation of Five- and Six-Membered Rings Promoted by Cuprous Ion",

abstract = "Copper(I) salts, especially the triflate and trifluoroacetate, promote efficient cleavage of 1-hydroxy-2-[bis- (phenylthio)methyl]cyclohexane and cyclopentane; a cyclic intermediate is unlikely, as complete reaction requires more than 2 mol equiv of copper(I); the product contains aldehyde and latent aldehyde units.",

author = "Semmelhack, \{M. F.\} and Tomesch, \{J. C.\}",

year = "1977",

month = jul,

day = "1",

doi = "10.1021/jo00435a039",

language = "English (US)",

volume = "42",

pages = "2657--2658",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

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TY - JOUR

T1 - Grob-Type Fragmentation of Five- and Six-Membered Rings Promoted by Cuprous Ion

AU - Semmelhack, M. F.

AU - Tomesch, J. C.

PY - 1977/7/1

Y1 - 1977/7/1

N2 - Copper(I) salts, especially the triflate and trifluoroacetate, promote efficient cleavage of 1-hydroxy-2-[bis- (phenylthio)methyl]cyclohexane and cyclopentane; a cyclic intermediate is unlikely, as complete reaction requires more than 2 mol equiv of copper(I); the product contains aldehyde and latent aldehyde units.

AB - Copper(I) salts, especially the triflate and trifluoroacetate, promote efficient cleavage of 1-hydroxy-2-[bis- (phenylthio)methyl]cyclohexane and cyclopentane; a cyclic intermediate is unlikely, as complete reaction requires more than 2 mol equiv of copper(I); the product contains aldehyde and latent aldehyde units.

UR - https://www.scopus.com/pages/publications/33847090212

UR - https://www.scopus.com/pages/publications/33847090212#tab=citedBy

U2 - 10.1021/jo00435a039

DO - 10.1021/jo00435a039

M3 - Letter

AN - SCOPUS:33847090212

SN - 0022-3263

VL - 42

SP - 2657

EP - 2658

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Grob-Type Fragmentation of Five- and Six-Membered Rings Promoted by Cuprous Ion

Abstract

All Science Journal Classification (ASJC) codes

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