A new reaction of diazomethane with norbornyl α-diketones

Faiz Ahmed Khan; Rashmirekha Satapathy; Ch Sudheer; Ch Nageswara Rao

doi:10.1016/j.tetlet.2005.08.087

A new reaction of diazomethane with norbornyl α-diketones

Faiz Ahmed Khan
, Rashmirekha Satapathy
, Ch Sudheer
, Ch Nageswara Rao

Chemistry (Twin Cities)

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

9 Scopus citations

Abstract

A new reaction of diazomethane with norbornyl α-diketones in MeOH as solvent leading regioselectively to ketals is described. The mechanistic details of this intriguing reaction were investigated employing d₄-MeOH, EtOH and d₆-EtOH. The surprising observation of complete deuterium incorporation in the diazomethane-derived methoxy group was accounted for by sequential deuterium exchange between the initially formed hemiketal d ₄-18 and diazomethane in the presence of d₄-MeOH as solvent.

Original language	English (US)
Pages (from-to)	7193-7196
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2005.08.087
State	Published - Oct 17 2005

Bibliographical note

Funding Information:
This work was supported by the Department of Science and Technology (DST), New Delhi. F.A.K. acknowledges the DST for a Swarnajayanti Fellowship. R.S., C.S. and C.N.R. thank CSIR/UGC for fellowships.

Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.

Keywords

Diazomethane
Ketal
Oxiranes
Regioselectivity
α-Diketones

Publisher link

10.1016/j.tetlet.2005.08.087

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title = "A new reaction of diazomethane with norbornyl α-diketones",

abstract = "A new reaction of diazomethane with norbornyl α-diketones in MeOH as solvent leading regioselectively to ketals is described. The mechanistic details of this intriguing reaction were investigated employing d4-MeOH, EtOH and d6-EtOH. The surprising observation of complete deuterium incorporation in the diazomethane-derived methoxy group was accounted for by sequential deuterium exchange between the initially formed hemiketal d 4-18 and diazomethane in the presence of d4-MeOH as solvent.",

keywords = "Diazomethane, Ketal, Oxiranes, Regioselectivity, α-Diketones",

author = "Khan, \{Faiz Ahmed\} and Rashmirekha Satapathy and Ch Sudheer and Rao, \{Ch Nageswara\}",

note = "Funding Information: This work was supported by the Department of Science and Technology (DST), New Delhi. F.A.K. acknowledges the DST for a Swarnajayanti Fellowship. R.S., C.S. and C.N.R. thank CSIR/UGC for fellowships. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2005.08.087",

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AU - Khan, Faiz Ahmed

AU - Satapathy, Rashmirekha

AU - Sudheer, Ch

AU - Rao, Ch Nageswara

N1 - Funding Information: This work was supported by the Department of Science and Technology (DST), New Delhi. F.A.K. acknowledges the DST for a Swarnajayanti Fellowship. R.S., C.S. and C.N.R. thank CSIR/UGC for fellowships. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2005/10/17

Y1 - 2005/10/17

N2 - A new reaction of diazomethane with norbornyl α-diketones in MeOH as solvent leading regioselectively to ketals is described. The mechanistic details of this intriguing reaction were investigated employing d4-MeOH, EtOH and d6-EtOH. The surprising observation of complete deuterium incorporation in the diazomethane-derived methoxy group was accounted for by sequential deuterium exchange between the initially formed hemiketal d 4-18 and diazomethane in the presence of d4-MeOH as solvent.

AB - A new reaction of diazomethane with norbornyl α-diketones in MeOH as solvent leading regioselectively to ketals is described. The mechanistic details of this intriguing reaction were investigated employing d4-MeOH, EtOH and d6-EtOH. The surprising observation of complete deuterium incorporation in the diazomethane-derived methoxy group was accounted for by sequential deuterium exchange between the initially formed hemiketal d 4-18 and diazomethane in the presence of d4-MeOH as solvent.

KW - Diazomethane

KW - Ketal

KW - Oxiranes

KW - Regioselectivity

KW - α-Diketones

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UR - https://www.scopus.com/pages/publications/24944552863#tab=citedBy

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DO - 10.1016/j.tetlet.2005.08.087

M3 - Article

AN - SCOPUS:24944552863

SN - 0040-4039

VL - 46

SP - 7193

EP - 7196

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

A new reaction of diazomethane with norbornyl α-diketones

Abstract

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Keywords

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