Thermolysis of spiro[2.4]heptadiene-4,6

J.M.E. Krekels; J.W. Haan, de; H. Kloosterziel

doi:10.1016/S0040-4039(01)98332-7

Thermolysis of spiro[2.4]heptadiene-4,6

J.M.E. Krekels
, J.W. Haan, de
, H. Kloosterziel

Chemical Engineering and Chemistry

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

31 Citations (Scopus)

Abstract

The thermolysis of spiro[2.4]hepta-4,6-diene (I) gave 6-methylfulvene, II, III, and IV. The conversion of I to 6-methylfulvene occurred in 2 steps via a biradical; an alternative second step gave 5-vinylcyclopentadiene which isomerized to II and III by 1,5-H shifts. A one-step sigmatropic 1,5-shift of an alkyl group in I, and a subsequent 1,5-H shift gave V. Electrocyclic opening of the cyclobutene ring in V then gave IV. [on SciFinder (R)]

Original language	English
Pages (from-to)	2751-2754
Number of pages	4
Journal	Tetrahedron Letters
Volume	11
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(01)98332-7
Publication status	Published - 1970

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title = "Thermolysis of spiro[2.4]heptadiene-4,6",

abstract = "The thermolysis of spiro[2.4]hepta-4,6-diene (I) gave 6-methylfulvene, II, III, and IV. The conversion of I to 6-methylfulvene occurred in 2 steps via a biradical; an alternative second step gave 5-vinylcyclopentadiene which isomerized to II and III by 1,5-H shifts. A one-step sigmatropic 1,5-shift of an alkyl group in I, and a subsequent 1,5-H shift gave V. Electrocyclic opening of the cyclobutene ring in V then gave IV. [on SciFinder (R)]",

author = "J.M.E. Krekels and \{Haan, de\}, J.W. and H. Kloosterziel",

year = "1970",

doi = "10.1016/S0040-4039(01)98332-7",

language = "English",

volume = "11",

pages = "2751--2754",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "32",

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T1 - Thermolysis of spiro[2.4]heptadiene-4,6

AU - Krekels, J.M.E.

AU - Haan, de, J.W.

AU - Kloosterziel, H.

PY - 1970

Y1 - 1970

N2 - The thermolysis of spiro[2.4]hepta-4,6-diene (I) gave 6-methylfulvene, II, III, and IV. The conversion of I to 6-methylfulvene occurred in 2 steps via a biradical; an alternative second step gave 5-vinylcyclopentadiene which isomerized to II and III by 1,5-H shifts. A one-step sigmatropic 1,5-shift of an alkyl group in I, and a subsequent 1,5-H shift gave V. Electrocyclic opening of the cyclobutene ring in V then gave IV. [on SciFinder (R)]

AB - The thermolysis of spiro[2.4]hepta-4,6-diene (I) gave 6-methylfulvene, II, III, and IV. The conversion of I to 6-methylfulvene occurred in 2 steps via a biradical; an alternative second step gave 5-vinylcyclopentadiene which isomerized to II and III by 1,5-H shifts. A one-step sigmatropic 1,5-shift of an alkyl group in I, and a subsequent 1,5-H shift gave V. Electrocyclic opening of the cyclobutene ring in V then gave IV. [on SciFinder (R)]

U2 - 10.1016/S0040-4039(01)98332-7

DO - 10.1016/S0040-4039(01)98332-7

M3 - Article

SN - 0040-4039

VL - 11

SP - 2751

EP - 2754

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Thermolysis of spiro[2.4]heptadiene-4,6

Abstract

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