7 Gosh, that was some ugly chemdraw, wasn't it. And not entirely accurate either, since the Lewis acid is definitely needed. (comment edited Oct 25 '18 at 21:29)
source | link

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

MechanismGeneration of t-butyl cation from pivaloyl chloride with Lewis acid

The t-butyl carbocation isn't as stable as the acylium cation (which is stabilised by resonance), but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium), it is enough to make it the main reaction route (insteadinstead of a side route).

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

The t-butyl carbocation isn't as stable as the acylium cation (which is stabilised by resonance), but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of a side route).

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Generation of t-butyl cation from pivaloyl chloride with Lewis acid

The t-butyl carbocation isn't as stable as the acylium cation (which is stabilised by resonance), but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium), it is enough to make it the main reaction route instead of a side route.

6 added 128 characters in body
source | link

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

The t-butyl carbocation isn't as stable as the acylium cation (which is stabilised by resonance), but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of a side route).

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

The t-butyl carbocation isn't as stable as the acylium cation, but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of a side route).

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

The t-butyl carbocation isn't as stable as the acylium cation (which is stabilised by resonance), but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of a side route).

5 added 9 characters in body
source | link

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts withas an acylated compoundelectrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

The t-butyl carbocation isn't as stable as the acylium cation, but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of a side route).

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts with an acylated compound decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

t-butyl isn't as stable as acylium cation, but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of side route).

You were on right path; tert-butyl carbocation is quite stable$\ldots$ so stable that the acylium cation, which normally reacts as an electrophile itself, instead decomposes via decarbonylation (loss of stable carbon monoxide molecule).

Mechanism

The t-butyl carbocation isn't as stable as the acylium cation, but the difference is small enough that with the help of the non-reversibility of CO loss (which is removed from the mixture as a gas) and reduction of the steric strain (which is lower in t-butyl than in acylium) it is enough to make it the main reaction route (instead of a side route).

4 added 71 characters in body
source | link
3 edited body
source | link
2 I no like HyphenOverflow.
source | link
1
source | link