Reactions of α-chloronitrones with unsaturated ethers

Shlomo Levinger; Shimon Shatzmiller

doi:10.1016/0040-4020(78)80053-2

Reactions of α-chloronitrones with unsaturated ethers

Shlomo Levinger, Shimon Shatzmiller

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

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Abstract

The Ag⁺ induced reaction of α-chloronitrones with unsaturated ethers goes in two parallel competitive directions. On the one hand cycloadducts like 3 are formed and on the other hand oxonium ions like 4. Formation of analogous oxonium compounds occurs also when α-alkoxynitrones are treated with Et₃O⁺BF₄^- in 1,2-dichloroethane. Formation of oxonium compounds with the enol-ethers is practically irreversible and leads to enol-ether fragmentation. With the saturated ethers compounds like 25 were formed and were used as a potential source of N-alkyl-N-vinyl-nitrosonium ions.

Original language	English
Pages (from-to)	563-567
Number of pages	5
Journal	Tetrahedron
Volume	34
Issue number	5
DOIs	https://doi.org/10.1016/0040-4020(78)80053-2
State	Published - 1978
Externally published	Yes

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title = "Reactions of α-chloronitrones with unsaturated ethers",

abstract = "The Ag+ induced reaction of α-chloronitrones with unsaturated ethers goes in two parallel competitive directions. On the one hand cycloadducts like 3 are formed and on the other hand oxonium ions like 4. Formation of analogous oxonium compounds occurs also when α-alkoxynitrones are treated with Et3O+BF4- in 1,2-dichloroethane. Formation of oxonium compounds with the enol-ethers is practically irreversible and leads to enol-ether fragmentation. With the saturated ethers compounds like 25 were formed and were used as a potential source of N-alkyl-N-vinyl-nitrosonium ions.",

author = "Shlomo Levinger and Shimon Shatzmiller",

year = "1978",

doi = "10.1016/0040-4020(78)80053-2",

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AU - Shatzmiller, Shimon

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AB - The Ag+ induced reaction of α-chloronitrones with unsaturated ethers goes in two parallel competitive directions. On the one hand cycloadducts like 3 are formed and on the other hand oxonium ions like 4. Formation of analogous oxonium compounds occurs also when α-alkoxynitrones are treated with Et3O+BF4- in 1,2-dichloroethane. Formation of oxonium compounds with the enol-ethers is practically irreversible and leads to enol-ether fragmentation. With the saturated ethers compounds like 25 were formed and were used as a potential source of N-alkyl-N-vinyl-nitrosonium ions.

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Reactions of α-chloronitrones with unsaturated ethers

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