1-Chloro-1-octyne sodium triethylaluminum hydride → cis-3-Decene

HRID 982560Notes

Reaction equation

HRID 982560 reaction equation
Cl[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H-].C([Al](CC)CC)C.[Na+].Cl[C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]CC.[H-].C[Al](C)C.[Na+]>>[CH3:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[CH3:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 867446351-Chloro-1-octyne sodium triethylaluminum hydrideHCID 867446361-Chloro-1-dodecyne sodium trimethylaluminum hydride

Product 2

HCID 53627142-Tridecene, (2Z)-Yield 66%HCID 5362723cis-3-DeceneYield 72%

Procedure

A similar crossover experiment using the alpha-chloroalkenylalanates derived from 1-chloro-1-octyne/sodium triethylaluminum hydride and 1-chloro-1-dodecyne/sodium trimethylaluminum hydride produced (by GC examination of a hydrolyzed aliquot) only the intramolecular transfer products cis-3-decene (72%) and cis-2-tridecene (66%). Neither of the crossover adducts cis-3-tetradecene and cis-2-nonene was detected.

Sources & evidence

ORD record
ord-6085a23a737f4fc1bdce4f389c6da37c
Source dataset
uspto-grants-1991_02
Patent number
US04996340

Reaction notes

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