The reaction of methyl diazoacetate with 4,4-dimethyl-2-pentyn-1-al and related compounds

A. S. Medvedeva; M. M. Demina; A. I. Borisova; O. I. Margorskaya; I. D. Kalikhman; E. I. Brodskaya; N. S. Vyazankin

doi:10.1016/S0022-328X(00)81949-X

The reaction of methyl diazoacetate with 4,4-dimethyl-2-pentyn-1-al and related compounds

A. S. Medvedeva
, M. M. Demina
, A. I. Borisova
, O. I. Margorskaya
, I. D. Kalikhman
, E. I. Brodskaya
, N. S. Vyazankin

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

16 Scopus citations

Abstract

Methyl 2-diazo-3-hydroxy-6,6-dimethyl-4-heptynoate was prepared by treating 4,4-dimethyl-2-pentyn-1-al with methyl diazoacetate at room temperature in the absence of catalysts. In the case of related aldehydes, RCCCHO (R = n-Bu, Me₃Si, Et₃Si, Et₃Ge), this unusual reaction is partially or completely suppressed by a competing 1,3-cycloaddition process. The latter leads to a mixture of isomeric 3- and 4-formylpyrazole, one of which cyalodimerizes to form tricyclic hemiaminal.

Original language	English
Pages (from-to)	109-118
Number of pages	10
Journal	Journal of Organometallic Chemistry
Volume	231
Issue number	2
DOIs	https://doi.org/10.1016/S0022-328X(00)81949-X
State	Published - 18 May 1982
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(00)81949-X

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title = "The reaction of methyl diazoacetate with 4,4-dimethyl-2-pentyn-1-al and related compounds",

abstract = "Methyl 2-diazo-3-hydroxy-6,6-dimethyl-4-heptynoate was prepared by treating 4,4-dimethyl-2-pentyn-1-al with methyl diazoacetate at room temperature in the absence of catalysts. In the case of related aldehydes, RCCCHO (R = n-Bu, Me3Si, Et3Si, Et3Ge), this unusual reaction is partially or completely suppressed by a competing 1,3-cycloaddition process. The latter leads to a mixture of isomeric 3- and 4-formylpyrazole, one of which cyalodimerizes to form tricyclic hemiaminal.",

author = "Medvedeva, \{A. S.\} and Demina, \{M. M.\} and Borisova, \{A. I.\} and Margorskaya, \{O. I.\} and Kalikhman, \{I. D.\} and Brodskaya, \{E. I.\} and Vyazankin, \{N. S.\}",

year = "1982",

month = may,

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doi = "10.1016/S0022-328X(00)81949-X",

language = "English",

volume = "231",

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TY - JOUR

T1 - The reaction of methyl diazoacetate with 4,4-dimethyl-2-pentyn-1-al and related compounds

AU - Medvedeva, A. S.

AU - Demina, M. M.

AU - Borisova, A. I.

AU - Margorskaya, O. I.

AU - Kalikhman, I. D.

AU - Brodskaya, E. I.

AU - Vyazankin, N. S.

PY - 1982/5/18

Y1 - 1982/5/18

N2 - Methyl 2-diazo-3-hydroxy-6,6-dimethyl-4-heptynoate was prepared by treating 4,4-dimethyl-2-pentyn-1-al with methyl diazoacetate at room temperature in the absence of catalysts. In the case of related aldehydes, RCCCHO (R = n-Bu, Me3Si, Et3Si, Et3Ge), this unusual reaction is partially or completely suppressed by a competing 1,3-cycloaddition process. The latter leads to a mixture of isomeric 3- and 4-formylpyrazole, one of which cyalodimerizes to form tricyclic hemiaminal.

AB - Methyl 2-diazo-3-hydroxy-6,6-dimethyl-4-heptynoate was prepared by treating 4,4-dimethyl-2-pentyn-1-al with methyl diazoacetate at room temperature in the absence of catalysts. In the case of related aldehydes, RCCCHO (R = n-Bu, Me3Si, Et3Si, Et3Ge), this unusual reaction is partially or completely suppressed by a competing 1,3-cycloaddition process. The latter leads to a mixture of isomeric 3- and 4-formylpyrazole, one of which cyalodimerizes to form tricyclic hemiaminal.

UR - https://www.scopus.com/pages/publications/0346075254

U2 - 10.1016/S0022-328X(00)81949-X

DO - 10.1016/S0022-328X(00)81949-X

M3 - Article

AN - SCOPUS:0346075254

SN - 0022-328X

VL - 231

SP - 109

EP - 118

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 2

ER -

The reaction of methyl diazoacetate with 4,4-dimethyl-2-pentyn-1-al and related compounds

Abstract

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